Epoxyphenol derivatives and herbicides containing them as active ingredients

ABSTRACT

Novel compounds of the formula  1! are disclosed, wherein X is hydrogen, fluorine or chlorine; Y is fluorine, chlorine or bromine; R 1  is hydrogen or C 1  -C 3  alkyl; and R 2  and Q are various groups. Also disclosed are herbicidal compositions containing these compounds as active ingredients and methods for controlling unfavorable weeds by application of these compounds.

FIELD OF THE INVENTION

The present invention relates to novel epoxyphenol derivatives andherbicides containing them as active ingredients.

SUMMARY OF THE INVENTION

The present inventors have intensively studied to develop excellentherbicides and found that epoxyphenol derivatives represented by theformula 1! below have excellent herbicidal activity, thereby completingthe present invention.

That is, the present invention provides novel compounds of the formula:##STR1## (hereinafter referred to as the present compound(s)) wherein: Xis hydrogen, fluorine or chlorine;

Y is fluorine, chlorine or bromine;

R¹ is hydrogen or C₁ -C₃ alkyl;

R² is C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ alkoxy (C₁ -C₆) alkyl, C₁-C₆ alkoxy (C₁ -C₆) alkoxy (C₁ -C₆) alkyl, C₁ -C₆ alkylthio (C₁ -C₆)alkyl, C₃ -C₆ alkenyl, C₃ -C₆ haloalkenyl, C₃ -C₆ alkynyl, C₃ -C₆haloalkynyl or C₃ -C₆ cycloalkyl; or

R² is a group of the formula:

    --COR.sup.3

wherein R³ is C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, phenyl which may beoptionally substituted with at least one halogen atom, C₁ -C₃ alkylgroup or C₁ -C₃ alkoxy group; or a group of the formula:

    --NR.sup.4 R.sup.5

wherein R⁴ and R⁵ are independently hydrogen, C₁ -C₆ alkyl or C₁ -C₆haloalkyl; or

R² is a group of the formula: ##STR2## wherein n is an integer of 1 to5; R⁶ is hydrogen, halogen, C₁ -C₃ alkyl or C₁ -C₃ alkoxy; or

R² is a group of the formula:

    --CR.sup.7 R.sup.8 COOR.sup.9

wherein R⁷ and R⁸ are independently hydrogen or C₁ -C₃ alkyl; R⁹ ishydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl or C₃ -C₆ cycloalkyl; or

R² is a group of the formula:

    --SO.sub.2 R.sup.10

wherein R¹⁰ is C₁ -C₆ alkyl or C₁ -C₆ haloalkyl; or phenyl which may beoptionally substituted with at least one C₁ -C₃ alkyl group; and

--Q is one of the groups Q-1 to Q-13 of the following formulae: ##STR3##wherein A¹ and A² are independently oxygen or sulfur; B is oxygen,sulfur or methylene;

R¹¹ is C₁ -C₆ alkyl which may be optionally substituted with at leastone halogen atom; or C₃ -C₆ cycloalkyl which may be optionallysubstituted with at least one C₁ -C₃ alkyl group;

R¹² is chlorine, methyl or C₁ -C₃ alkoxy;

R¹³ is hydrogen, halogen or C₁ -C₃ alkyl;

R¹⁴ is C₁ -C₃ alkyl which may be substituted with at least one halogenatom;

R¹⁵ is hydrogen, C₁ -C₆ alkyl, C₃ -C₆ alkenyl, C₃ -C₆ alkynyl, amino orbenzyl;

R¹⁶ and R¹⁷ are independently hydrogen or C₁ -C₃ alkyl;

R¹⁸ is C₁ -C₆ alkyl which may be optionally substituted with at leastone halogen atom; C₃ -C₆ alkynyl which may be optionally substitutedwith at least one halogen atom; or C₃ -C₆ alkenyl which may beoptionally substituted with at least one halogen atom;

R¹⁹ is hydrogen or C₁ -C₆ alkyl which may be optionally substituted withat least one halogen atom; or C₇ -C₁₇ aralkyl or aryl;

R²⁰ is hydrogen or C₁ -C₆ alkyl which may be optionally substituted withat least one halogen atom;

R²¹ and R²² are independently hydrogen or halogen; or C₁ -C₆ alkyl whichmay be optionally substituted with at least one halogen atom; and

m is an integer of 1 or 2.

The present invention further provides herbicides containing the abovecompounds as active ingredients.

Some of the present compounds have optical isomers based on the presenceof at least one asymmetrical carbon atom, and these optical isomers are,of course, included within the scope of the present invention.

In the above definition of the present compounds, the respectivesubstituents are exemplified as follows:

Examples of the C₁ -C₃ alkyl represented by R¹ include methyl.

Examples of the C₁ -C₆ alkyl represented by R² include methyl, ethyl,isopropyl, sec-butyl and t-butyl.

Examples of the C₁ -C₆ haloalkyl represented by R² includedifluoromethyl and tetrafluoroethyl.

Examples of the C₁ -C₆ alkoxy (C₁ -C₆) alkyl represented by R² includemethoxymethyl, ethoxymethyl and methoxyethyl.

Examples of the C₁ -C₆ alkoxy (C₁ -C₆) alkoxy (C₁ -C₆) alkyl representedby R² include methoxyethoxymethyl.

Examples of the C₁ -C₆ alkylthio (C₁ -C₆) alkyl represented by R²include methylthiomethyl.

Examples of the C₃ -C₆ alkenyl represented by R² include allyl,1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl and2-methyl-3-butenyl.

Examples of the C₃ -C₆ haloalkenyl represented by R² include2-chloro-2-propenyl and 3,3-dichloro-2-propenyl.

Examples of the C₃ -C₆ alkynyl represented by R² include propargyl,1-methyl-2-propynyl, 2-butynyl and 1,1-dimethyl-2-propynyl.

Examples of the C₃ -C₆ haloalkynyl represented by R² include3-iodo-2-propynyl and 3-bromo-2-propynyl.

Examples of the C₃ -C₆ cycloalkyl represented by R² include cyclopropyl,cyclopentyl and cyclohexyl.

Examples of the group of the formula: --COR³, which is represented byR², include acetyl, propanoyl, trifluoroacetyl, chloroacetyl,2-methylpropanoyl, dichloroacetyl, pivaloyl, benzoyl, 4-methoxybenzoyland dimethylaminocarbonyl.

Examples of the group of the formula: ##STR4## which is represented byR², include benzyl and phenetyl.

Examples of the group of the formula: --CR⁷ R⁸ COOR⁹, which isrepresented by R², include methoxycarbonylmethyl, ethoxycarbonylmethyl,n-amyloxycarbonylmethyl, isopropoxycarbonylmethyl,1-methoxycarbonylethyl, cyclopentyloxycarbonylmethyl andcyclohexyloxycarbonylmethyl.

Examples of the group of the formula: --SO₂ R¹⁰, which is represented byR², include methanesulfonyl, ethanesulfonyl, chloromethanesulfonyl,benzenesulfonyl and 4-toluenesulfonyl.

Examples of the C₁ -C₆ alkyl optionally substituted with at least onehalogen atom, which is represented by R¹¹, include methyl, isopropyl andtert-butyl.

Examples of the C₃ -C₆ cycloalkyl optionally substituted with at leastone C₁ -C₃ alkyl group, which is represented by R¹¹, include1-methylcyclopropyl.

Examples of the C₁ -C₃ alkoxy represented by R¹² include methoxy.

Examples of the halogen represented by R¹³ include chlorine.

Examples of the C₁ -C₃ alkyl represented by R¹³ include methyl.

Examples of the C₁ -C₃ alkyl optionally substituted with at least onehalogen atom, which is represented by R¹⁴, include trifluoromethyl andpentafluoroethyl.

Examples of the C₁ -C₆ alkyl represented by R¹⁵ include methyl.

Examples of the C₃ -C₆ alkenyl represented by R¹⁵ include allyl.

Examples of the C₃ -C₆ alkynyl represented by R¹⁵ include propargyl.

Examples of the C₁ -C₃ alkyl represented by R¹⁶ and R¹⁷ include methyl.

Examples of the C₁ -C₆ alkyl optionally substituted with at least onehalogen atom, which is represented by R¹⁸, include methyl.

Examples of the C₃ -C₆ alkynyl optionally substituted with at least onehalogen atom, which is represented by R¹⁸, include propargyl.

Examples of the C₃ -C₆ alkenyl optionally substituted with at least onehalogen atom, which is represented by R¹⁸, include allyl.

Examples of the C₁ -C₆ alkyl optionally substituted with at least onehalogen atom, which is represented by R¹⁹, include methyl andtrifluoromethyl.

Examples of the C₇ -C₁₇ aralkyl represented by R¹⁹ include benzyl.

Examples of the aryl represented by R¹⁹ include phenyl.

Examples of the C₁ -C₆ alkyl optionally substituted with at least onehalogen atom, which is represented by R²⁰, include methyl.

Examples of the halogen represented by R²¹ and R²² include chlorine.

Examples of the C₁ -C₆ alkyl optionally substituted with at least onehalogen atom, which is represented by R²¹ and R²², include methyl.

From the viewpoint of herbicidal activity, preferred substituentsrepresented by R¹ are hydrogen and methyl, and preferred substituentsrepresented by R² are acetyl, benzoyl, methylthiomethyl andmethoxymethyl.

Preferred compounds are those wherein X is fluorine, Y is chlorine, R¹is methyl, R² is acetyl or methylthiomethyl,--Q is a group of theformula Q-8, A¹ is oxygen, R¹³ is hydrogen, R¹⁴ is trifluoromethyl, andR¹⁵ is methyl.

The present compounds can be produced by, for example, a processcomprising reacting an allylphenol derivative of the formula: ##STR5##wherein X, Y, Q, R¹ and R² are each as defined above, with anepoxidizing agent.

The reaction is usually effected in a solvent. The reaction temperatureis usually in the range of -20° to 150° C., preferably 0° to 50° C. Thereaction time is usually in the range of a moment to 48 hours. Theamount of the epoxidizing agent to be used in the reaction is usually 1to 5 moles per mole of the compound 2!.

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as petroleum ether and hexane; fatty acids such as formic acid andacetic acid; and halogenated hydrocarbons such as methylene chloride,chloroform and 1,2-dichloroethane. Examples of the epoxidizing agentinclude peracids such as perbenzoic acid, m-chloroperbenzoic acid,peracetic acid and trifluoroperacetic acid; and mixtures thereof.

After completion of the reaction, the reaction mixture is treated, ifnecessary, with a reducing agent such as aqueous sodium thiosulfatesolution or aqueous sodium hydrogensulfite solution to remove excessepoxidizing agent, followed by ordinary post-treatments such asextraction with an organic solvent and concentration, and if necessary,subsequent purification such as chromatography or recrystallization.Thus, the present compounds can be isolated.

Some of the present compounds can be produced by introducing an R²moiety into a phenol derivative of the formula: ##STR6## wherein X, Y, Qand R¹ are each as defined above. The method for introducing the R²moiety includes the following methods (a), (b) and (c), which areselected depending upon the R².

(a) The present compounds wherein R² is C₁ -C₆ alkoxymethyl or C₁ -C₆alkoxy (C₁ -C₆) alkoxymethyl can be produced by reacting the compound 3!with a compound of the formula:

    R.sup.21 --L                                                4!

wherein R²¹ is C₁ -C₆ alkoxymethyl or C₁ -C₆ alkoxy (C₁ -C₆)alkoxymethyl; and L is chlorine, bromine or iodine, methanesulfonyloxyor p-toluenesulfonyloxy.

The reaction is usually effected in a solvent in the presence of a base.The reaction temperature is usually in the range of <20° to 100° C. orthe refluxing temperature of the solvent. The reaction time is usuallyin the range of a moment to 48 hours. The amounts of the reagents to beused in the reaction are usually 1 to 5 moles of the compound 4! andusually 1 mole to an excess of the base, per mole of the compound 3!.

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as hexane, heptane, ligroin and petroleum ether; aromatichydrocarbons such as benzene, toluene and xylene; halogenatedhydrocarbons such as chloroform, carbon tetrachloride, dichloroethane,chlorobenzene and dichlorobenzene; ethers such as diethyl ether,diisopropyl ether, dioxane, tetrahydrofuran and ethylene glycol dimethylether; ketones such as acetone, methyl ethyl ketone, methyl isobutylketone, isophorone and cyclohexanone; esters such as ethyl formate,ethyl acetate, butyl acetate and diethyl carbonate; nitro compounds suchas nitromethane and nitrobenzene; nitriles such as acetonitrile andisobutyronitrile; acid amides such as N,N-dimethylformamide andacetamide; tertiary amines such as pyridine, triethylamine,N,N-dimethylaniline, N,N-diethylaniline and N-methylmorpholine; sulfurcompounds such as dimethylsulfoxide and sulfolane; and mixtures thereof.

Examples of the base which can be used include organic bases such astriethylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridineand N,N-dimethylaniline; and mixtures thereof.

After completion of the reaction, the reaction mixture is poured intowater and the precipitated crystals are collected by filtration, or thereaction mixture is subjected to ordinary post-treatments such asextraction with an organic solvent and concentration, followed by, ifnecessary, subsequent purification such as chromatography orrecrystallization. Thus, the present compounds can be isolated.

(b) The present compounds wherein R² is a group of the formula: --COR³can be produced by reacting the compound 3! with a compound of theformula:

    R.sup.3 CO--G                                               5!

wherein R³ is as defined above and G is chlorine or bromine, or with acompound of the formula:

    (R.sup.3 CO).sub.2 O                                        6!

wherein R³ is as defined above.

The reaction is usually effected without any solvent or in a solvent inthe presence of a base. The reaction temperature is usually in the rangeof <20° to 200° C., preferably 0° C. to the refluxing temperature of thesolvent when used, or preferably 0° to 100° C. in the absence ofsolvents. The reaction time is usually in the range of a moment to 24hours. The amounts of the reagents to be used in the reaction areusually 1 mole to a large excess of the compound 5! or 6! and usually 1mole to a large excess of the base, per mole of the compound 3!.

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as petroleum ether and hexane; aromatic hydrocarbons such astoluene and xylene; halogenated hydrocarbons such as chloroform,1,2-dichloroethane, chlorobenzene and o-dichlorobenzene; ethers such asdiethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran andethylene glycol dimethyl ether; ketones such as acetone, methyl isobutylketone and cyclohexanone; esters such as ethyl acetate and diethylcarbonate; nitro compounds such as nitroethane and nitrobenzene;nitriles such as acetonitrile and isobutyronitrile; tertiary amines suchas pyridine, triethylamine, N,N-dimethylaniline, N,N-diethylaniline andN-methylmorpholine; acid amides such as formamide, N,N-dimethylformamideand acetamide; sulfur compounds such as dimethylsulfoxide and sulfolane;and mixtures thereof.

Examples of the base which can be used include organic bases such astriethylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridineand N,N-dimethylaniline; and mixtures thereof.

After completion of the reaction, the reaction mixture is concentratedor poured into water, and the precipitated crystals are collected byfiltration, or the reaction mixture is subjected to ordinarypost-treatments such as extraction with an organic solvent andconcentration, followed by, if necessary, subsequent purification suchas chromatography or recrystallization. Thus, the present compounds canbe isolated.

(c) The present compounds wherein R² is methylthiomethyl can be producedby reacting the compound 3! with acetic anhydride and dimethylsulfoxide.

The reaction is usually effected without any solvent or in a solvent.The reaction temperature is usually in the range of 0° to 100° C. Thereaction time is usually in the range of a moment to 24 hours. Themounts of the reagents to be used in the reaction are usually 1 mole toa large excess of acetic anhydride and usually 1 mole to a large excessof dimethylsulfoxide, per mole of the compound 3!.

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as hexane, heptane, ligroin and petroleum ether; aromatichydrocarbons such as benzene, toluene and xylene; halogenatedhydrocarbons such as chloroform, carbon tetrachloride, dichloroethane,chlorobenzene and dichlorobenzene; ethers such as diethyl ether,diisopropyl ether, dioxane, tetrahydrofuran and ethylene glycol dimethylether; ketones such as acetone, methyl ethyl ketone, methyl isobutylketone, isophorone and cyclohexanone; esters such as ethyl formate,ethyl acetate, butyl acetate and diethyl carbonate; nitro compounds suchas nitromethane and nitrobenzene; nitriles such as acetonitrile andisobutyronitrile; acid amides such as formamide, N,N-dimethylformamideand acetamide; sulfur compounds such as dimethylsulfoxide and sulfolane;and mixtures thereof.

After completion of the reaction, the reaction mixture is poured intowater, and the precipitated crystals are collected by filtration, or thereaction mixture is concentrated or subjected to ordinarypost-treatments such as extraction with an organic solvent andconcentration, followed by, if necessary, subsequent purification suchas chromatography or recrystallization. Thus, the present compounds canbe isolated.

Examples of the present compounds are shown in Tables 1 to 13 below;however, the present compounds are not limited to these examples. InTables 1 to 13, "c C₅ H₉ ", "c C₆ H₁₁ ", "^(n) C₄ H₉ ", "^(n) C₅ H₁₁ ","p-CH₃ OC₆ H₄ ", "p-CH₃ C₆ H₄ " and "p-ClC₆ H₄ " mean cyclopentyl,cyclohexyl, normal butyl, normal pentyl, p-methoxyphenyl, p-methylphenyland p-chlorophenyl, respectively.

                  TABLE 1                                                         ______________________________________                                         ##STR7##                                                                     Compound                                                                      No.        X      Y      R.sup.1                                                                             R.sup.2                                        ______________________________________                                        1-1        F      Cl     H     CH.sub.3                                       1-2        F      Cl     H     C.sub.2 H.sub.5                                1-3        F      Cl     H     (CH.sub.3).sub.2 CH                            1-4        F      Cl     H     (CH.sub.3).sub.3 C                             1-5        F      Cl     H     ClCH.sub.2 CH.sub.2                            1-6        F      Cl     H     CH.sub.3 OCH.sub.2                             1-7        F      Cl     H     C.sub.2 H.sub.5 OCH.sub.2                      1-8        F      Cl     H     CH.sub.3 OCH.sub.2 CH.sub.2                    1-9        F      Cl     H     CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          1-10       F      Cl     H     CH.sub.3 SCH.sub.2                             1-11       F      Cl     H     CH.sub.2 CHCH.sub.2                            1-12       F      Cl     H     CH.sub.2 CHCH.sub.2 CH.sub.2                   1-13       F      Cl     H     CH.sub.3 CHCHCH.sub.2                          1-14       F      Cl     H     CH.sub.2 CClCH.sub.2                           1-15       F      Cl     H     CCl.sub.2 CHCH.sub.2                           1-16       F      Cl     H     CHCCH.sub.2                                    1-17       F      Cl     H     CHCCH(CH.sub.3)                                1-18       F      Cl     H     BrCCCH.sub.2                                   1-19       F      Cl     H     cC.sub.5 H.sub.9                               1-20       F      Cl     H     cC.sub.6 H.sub.11                              1-21       F      Cl     H     CH.sub.3 CO                                    1-22       F      Cl     H     C.sub.2 H.sub.5 CO                             1-23       F      Cl     H     (CH.sub.3).sub.2 CHCO                          1-24       F      Cl     H     (CH.sub.3).sub.3 CCO                           1-25       F      Cl     H     C.sub.6 H.sub.5 CO                             1-26       F      Cl     H     p-CH.sub.3 OC.sub.6 H.sub.4 CO                 1-27       F      Cl     H     p-CH.sub.3 C.sub.6 H.sub.4 CO                  1-28       F      Cl     H     ClCH.sub.2 CO                                  1-29       F      Cl     H     CH.sub.3 NHCO                                  1-30       F      Cl     H     (CH.sub.3).sub.2 NCO                           1-31       F      Cl     H     (C.sub.2 H.sub.5).sub.2 NCO                    1-32       F      Cl     H     C.sub.6 H.sub.5 CH.sub.2                       1-33       F      Cl     H     p-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2           1-34       F      Cl     H     p-ClC.sub.6 H.sub.4 CH.sub.2                   1-35       F      Cl     H     C.sub.6 H.sub.5 CH.sub.2 CH.sub.2              1-36       F      Cl     H     CH.sub.3 OOCCH.sub.2                           1-37       F      Cl     H     C.sub.2 H.sub.5 OOCCH.sub.2                    1-38       F      Cl     H     (CH.sub.3).sub.2 CHOOCCH.sub.2                 1-39       F      Cl     H     .sup.n C.sub.4 H.sub.9 OOCCH.sub.2             1-40       F      Cl     H     .sup.n C.sub.5 H.sub.11 OOCCH.sub.2            1-41       F      Cl     H     CH.sub.3 OOCCH(CH.sub.3)                       1-42       F      Cl     H     C.sub.2 H.sub.5 OOCCH(CH.sub.3)                1-43       F      Cl     H     cC.sub.5 H.sub.9 OOCCH.sub.2                   1-44       F      Cl     H     cC.sub.6 H.sub.11 OOCCH.sub.2                  1-45       F      Cl     H     CH.sub.3 SO.sub.2                              1-46       F      Cl     H     C.sub.2 H.sub.5 SO.sub.2                       1-47       F      Cl     H     (CH.sub.3).sub.2 CHSO.sub.2                    1-48       F      Cl     H     ClCH.sub.2 SO.sub.2                            1-49       F      Cl     H     C.sub.6 H.sub.5 SO.sub.2                       1-50       F      Cl     H     p-CH.sub.3 C.sub.6 H.sub.4 SO.sub.2            1-51       F      Cl     CH.sub.3                                                                            CH.sub.3                                       1-52       F      Cl     CH.sub.3                                                                            C.sub.2 H.sub.5                                1-53       F      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 CH                            1-54       F      Cl     CH.sub.3                                                                            (CH.sub.3).sub.3 C                             1-55       F      Cl     CH.sub.3                                                                            ClCH.sub.2 CH.sub.2                            1-56       F      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2                             1-57       F      Cl     CH.sub.3                                                                            C.sub.2 H.sub.5 OCH.sub.2                      1-58       F      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2 CH.sub.2                    1-59       F      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          1-60       F      Cl     CH.sub.3                                                                            CH.sub.3 SCH.sub.2                             1-61       F      Cl     CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                            1-62       F      Cl     CH.sub.3                                                                            CH.sub.2 CHCH.sub.2 CH.sub.2                   1-63       F      Cl     CH.sub.3                                                                            CH.sub.3 CHCHCH.sub.2                          1-64       F      Cl     CH.sub.3                                                                            CH.sub.2 CClCH.sub.2                           1-65       F      Cl     CH.sub.3                                                                            CCl.sub.2 CHCH.sub.2                           1-66       F      Cl     CH.sub.3                                                                            CHCCH.sub.2                                    1-67       F      Cl     CH.sub.3                                                                            CHCC(CH.sub.3)                                 1-68       F      Cl     CH.sub.3                                                                            BrCCHCH.sub.2                                  1-69       F      Cl     CH.sub.3                                                                            cC.sub.5 H.sub.9                               1-70       F      Cl     CH.sub.3                                                                            cC.sub.6 H.sub.11                              1-71       F      Cl     CH.sub.3                                                                            CH.sub.3 CO                                    1-72       F      Cl     CH.sub.3                                                                            C.sub.2 H.sub.5 CO                             1-73       F      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 CHCO                          1-74       F      Cl     CH.sub.3                                                                            (CH.sub.3).sub.3 CCO                           1-75       F      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CO                             1-76       F      Cl     CH.sub.3                                                                            p-CH.sub.3 OC.sub.6 H.sub.4 CO                 1-77       F      Cl     CH.sub.3                                                                            p-CH.sub.3 C.sub.6 H.sub.5 CO                  1-78       F      Cl     CH.sub.3                                                                            ClCH.sub.2 CO                                  1-79       F      Cl     CH.sub.3                                                                            CH.sub.3 NHCO                                  1-80       F      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 NCO                           1-81       F      Cl     CH.sub.3                                                                            (C.sub.2 H.sub.5).sub.2 NCO                    1-82       F      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CH.sub.2                       1-83       F      Cl     CH.sub.3                                                                            p-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2           1-84       F      Cl     CH.sub.3                                                                            p-ClC.sub.6 H.sub.4 CH.sub.2                   1-85       F      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CH.sub.2 CH.sub.2              1-86       F      Cl     CH.sub.3                                                                            CH.sub.3 OOCCH.sub.2                           1-87       F      Cl     CH.sub.3                                                                            C.sub.2 H.sub.5 OOCCH.sub.2                    1-88       F      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 CHOOCCH.sub.2                 1-89       F      Cl     CH.sub.3                                                                            .sup.n C.sub.4 H.sub.9 OOCCH.sub.2             1-90       F      Cl     CH.sub.3                                                                            .sup.n C.sub.5 H.sub.11 OOCCH.sub.2            1-91       F      Cl     CH.sub.3                                                                            CH.sub.3 OOCCH(CH.sub.3)                       1-92       F      Cl     CH.sub.3                                                                            C.sub.2 H.sub.5 OOCCH(CH.sub.3)                1-93       F      Cl     CH.sub.3                                                                            cC.sub.5 H.sub.9 OOCCH.sub.2                   1-94       F      Cl     CH.sub.3                                                                            cC.sub.6 H.sub.11 OOCCH.sub.2                  1-95       F      Cl     CH.sub.3                                                                            CH.sub.3 SO.sub.2                              1-96       F      Cl     CH.sub.3                                                                            C.sub.2 H.sub.5 SO.sub.2                       1-97       F      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 CHSO.sub.2                    1-98       F      Cl     CH.sub.3                                                                            ClCH.sub.2 SO.sub.2                            1-99       F      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 SO.sub.2                       1-100      F      Cl     CH.sub.3                                                                            p-CH.sub.3 C.sub.6 H.sub.4 SO.sub.2            1-101      H      Cl     H     CH.sub.3                                       1-102      H      Cl     H     C.sub.2 H.sub.5                                1-103      H      Cl     H     (CH.sub.3).sub.2 CH                            1-104      H      Cl     H     (CH.sub.3).sub.3 C                             1-105      H      Cl     H     ClCH.sub.2 CH.sub.2                            1-106      H      Cl     H     CH.sub.3 OCH.sub.2                             1-107      H      Cl     H     C.sub.2 H.sub.5 OCH.sub.2                      1-108      H      Cl     H     CH.sub.3 OCH.sub.2 CH.sub.2                    1-109      H      Cl     H     CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          1-110      H      Cl     H     CH.sub.3 SCH.sub.2                             1-111      H      Cl     H     CH.sub.2 CHCH.sub.2                            1-112      H      Cl     H     CH.sub.2 CHCH.sub.2 CH.sub.2                   1-113      H      Cl     H     CH.sub.3 CHCHCH.sub.2                          1-114      H      Cl     H     CH.sub.2 CClCH.sub.2                           1-115      H      Cl     H     CCl.sub.2 CHCH.sub.2                           1-116      H      Cl     H     CHCCH.sub.2                                    1-117      H      Cl     H     CHCCH(CH.sub.3)                                1-118      H      Cl     H     BrCCCH.sub.2                                   1-119      H      Cl     H     cC.sub.5 H.sub.9                               1-120      H      Cl     H     cC.sub.6 H.sub.11                              1-121      H      Cl     H     CH.sub.3 CO                                    1-122      H      Cl     H     C.sub.2 H.sub.5 CO                             1-123      H      Cl     H     (CH.sub.3).sub.2 CHCO                          1-124      H      Cl     H     (CH.sub.3).sub.3 CCO                           1-125      H      Cl     H     C.sub.6 H.sub.5 CO                             1-126      H      Cl     H     p-CH.sub.3 OC.sub.6 H.sub.4 CO                 1-127      H      Cl     H     p-CH.sub.3 C.sub.6 H.sub.5 CO                  1-128      H      Cl     H     ClCH.sub.2 CO                                  1-129      H      Cl     H     CH.sub.3 NHCO                                  1-130      H      Cl     H     (CH.sub.3).sub.2 NCO                           1-131      H      Cl     H     (C.sub.2 H.sub.5).sub.2 NCO                    1-132      H      Cl     H     C.sub.6 H.sub.5 CH.sub.2                       1-133      H      Cl     H     p-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2           1-134      H      Cl     H     p-ClC.sub.5 H.sub.4 CH.sub.2                   1-135      H      Cl     H     C.sub.6 H.sub.5 CH.sub.2 CH.sub.2              1-136      H      Cl     H     CH.sub.3 OOCCH.sub.2                           1-137      H      Cl     H     C.sub.2 H.sub.5 OOCCH.sub.2                    1-138      H      Cl     H     (CH.sub.3).sub.2 CHOOCCH.sub.2                 1-139      H      Cl     H     .sup.n C.sub.4 H.sub.9 OOCCH.sub.2             1-140      H      Cl     H     .sup.n C.sub.5 H.sub.11 OOCCH.sub.2            1-141      H      Cl     H     CH.sub.3 OOCCH(CH.sub.3)                       1-142      H      Cl     H     C.sub.2 H.sub.5 OOCCH(CH.sub.3)                1-143      H      Cl     H     cC.sub.5 H.sub.9 OOCCH.sub.2                   1-144      H      Cl     H     cC.sub.6 H.sub.11 OOCCH.sub.2                  1-145      H      Cl     H     CH.sub.3 SO.sub.2                              1-146      H      Cl     H     C.sub.2 H.sub.5 SO.sub.2                       1-147      H      Cl     H     (CH.sub.3).sub.2 CHSO.sub.2                    1-148      H      Cl     H     ClCH.sub.2 SO.sub.2                            1-149      H      Cl     H     C.sub.6 H.sub.5 SO.sub.2                       1-150      H      Cl     H     p-CH.sub.3 C.sub.5 H.sub.4 SO.sub.2            1-151      H      Cl     CH.sub.3                                                                            CH.sub.3                                       1-152      H      Cl     CH.sub.3                                                                            C.sub.2 H.sub.5                                1-153      H      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 CH                            1-154      H      Cl     CH.sub.3                                                                            (CH.sub.3).sub.3 C                             1-155      H      Cl     CH.sub.3                                                                            ClCH.sub.2 CH.sub.2                            1-156      H      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2                             1-157      H      Cl     CH.sub.3                                                                            C.sub.2 H.sub.5 OCH.sub.2                      1-158      H      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2 CH.sub.2                    1-159      H      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          1-160      H      Cl     CH.sub.3                                                                            CH.sub.3 SCH.sub.2                             1-161      H      Cl     CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                            1-162      H      Cl     CH.sub.3                                                                            CH.sub.2 CHCH.sub.2 CH.sub.2                   1-163      H      Cl     CH.sub.3                                                                            CH.sub.3 CHCHCH.sub.2                          1-164      H      Cl     CH.sub.3                                                                            CH.sub.2 CClCH.sub.2                           1-165      H      Cl     CH.sub.3                                                                            CCl.sub.2 CHCH.sub.2                           1-166      H      Cl     CH.sub.3                                                                            CHCCH.sub.2                                    1-167      H      Cl     CH.sub.3                                                                            CHCCH(CH.sub.3)                                1-168      H      Cl     CH.sub.3                                                                            BrCCCH.sub.2                                   1-169      H      Cl     CH.sub.3                                                                            cC.sub.5 H.sub.9                               1-170      H      Cl     CH.sub.3                                                                            cC.sub.6 H.sub.11                              1-171      H      Cl     CH.sub.3                                                                            CH.sub.3 CO                                    1-172      H      Cl     CH.sub.3                                                                            C.sub.2 H.sub.5 CO                             1-173      H      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 CHCO                          1-174      H      Cl     CH.sub.3                                                                            (CH.sub.3).sub.3 CCO                           1-175      H      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CO                             1-176      H      Cl     CH.sub.3                                                                            p-CH.sub.3 OC.sub.6 H.sub.4 CO                 1-177      H      Cl     CH.sub.3                                                                            p-CH.sub.3 C.sub.6 H.sub.5 CO                  1-178      H      Cl     CH.sub.3                                                                            ClCH.sub.2 CO                                  1-179      H      Cl     CH.sub.3                                                                            CH.sub.3 NHCO                                  1-180      H      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 NCO                           1-181      H      Cl     CH.sub.3                                                                            (C.sub.2 H.sub.5).sub.2 NCO                    1-182      H      Cl     H     C.sub.6 H.sub.5 CH.sub.2                       1-183      H      Cl     CH.sub.3                                                                            p-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2           1-184      H      Cl     CH.sub.3                                                                            p-ClC.sub.6 H.sub.4 CH.sub.2                   1-185      H      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CH.sub.2 CH.sub.2              1-186      H      Cl     CH.sub.3                                                                            CH.sub.3 OOCCH.sub.2                           1-187      H      Cl     CH.sub.3                                                                            C.sub.2 H.sub.5 OOCCH.sub.2                    1-188      H      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 CHOOCCH.sub.2                 1-189      H      Cl     CH.sub.3                                                                            .sup.n C.sub.4 H.sub.9 OOCCH.sub.2             1-190      H      Cl     CH.sub.3                                                                            .sup.n C.sub.5 H.sub.11 OOCCH.sub.2            1-191      H      Cl     CH.sub.3                                                                            CH.sub.3 OOCCH(CH.sub.3)                       1-192      H      Cl     CH.sub.3                                                                            C.sub.2 H.sub.5 OOCCH(CH.sub.3)                1-193      H      Cl     CH.sub.3                                                                            cC.sub.5 H.sub.9 OOCCH.sub.2                   1-194      H      Cl     CH.sub.3                                                                            cC.sub.6 H.sub.11 OOCCH.sub.2                  1-195      H      Cl     CH.sub.3                                                                            CH.sub.3 SO.sub.2                              1-196      H      Cl     CH.sub.3                                                                            C.sub.2 H.sub.5 SO.sub.2                       1-197      H      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 CHSO.sub.2                    1-198      H      Cl     CH.sub.3                                                                            ClCH.sub.2 SO.sub.2                            1-199      H      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 SO.sub.2                       1-200      H      Cl     CH.sub.3                                                                            p-CH.sub.3 C.sub.6 H.sub.4 SO.sub.2            1-201      F      Br     H     (CH.sub.3).sub.2 CH                            1-202      Cl     Cl     H     (CH.sub.3).sub.2 CH                            1-203      F      F      H     (CH.sub.3).sub.2 CH                            ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                         ##STR8##                                                                     Compound                                                                      No.     X      Y      A.sup.1                                                                            A.sup.2                                                                           R.sup.1                                                                            R.sup.2                                   ______________________________________                                        2-1     F      Cl     O    O   H    (CH.sub.3).sub.2 CH                       2-2     F      Cl     O    O   H    ClCH.sub.2 CH.sub.2                       2-3     F      Cl     O    O   H    CH.sub.3 OCH.sub.2                        2-4     F      Cl     O    O   H    CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2                                         5                                         2-5     F      Cl     O    O   H    CH.sub.3 SCH.sub.2                        2-6     F      Cl     O    O   H    CH.sub.2 CHCH.sub.2                       2-7     F      Cl     O    O   H    CH.sub.2 CClCH.sub.2                      2-8     F      Cl     O    O   H    CH CCH.sub.2                              2-9     F      Cl     O    O   H    CH CCH(CH.sub.3)                          2-10    F      Cl     O    O   H    cC.sub.5 H.sub.9                          2-11    F      Cl     O    O   H    CH.sub.3 CO                               2-12    F      Cl     O    O   H    CH.sub.3 NHCO                             2-13    F      Cl     O    O   H    C.sub.6 H.sub.5 CO                        2-14    F      Cl     O    O   H    C.sub.6 H.sub.5 CH.sub.2                  2-15    F      Cl     O    O   H    CH.sub.3 OOCCH.sub.2                      2-16    F      Cl     O    O   H    CH.sub.3 SO.sub.2                         2-17    F      Cl     O    O   CH.sub.3                                                                           (CH.sub.3).sub.2 CH                       2-18    F      Cl     O    O   CH.sub.3                                                                           ClCH.sub.2 CH.sub.2                       2-19    F      Cl     O    O   CH.sub.3                                                                           CH.sub.3 OCH.sub.2                        2-20    F      Cl     O    O   CH.sub.3                                                                           CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2                                         9                                         2-21    F      Cl     O    O   CH.sub.3                                                                           CH.sub.3 SCH.sub.2                        2-22    F      Cl     O    O   CH.sub.3                                                                           CH.sub.2 CHCH.sub.2                       2-23    F      Cl     O    O   CH.sub.3                                                                           CH.sub.2 CClCH.sub.2                      2-24    F      Cl     O    O   CH.sub.3                                                                           CH CCH.sub.2                              2-25    F      Cl     O    O   CH.sub.3                                                                           CH CCH(CH.sub.3)                          2-26    F      Cl     O    O   CH.sub.3                                                                           cC.sub.5 H.sub.9                          2-27    F      Cl     O    O   CH.sub.3                                                                           CH.sub.3 CO                               2-28    F      Cl     O    O   CH.sub.3                                                                           CH.sub.3 NHCO                             2-29    F      Cl     O    O   CH.sub.3                                                                           C.sub.6 H.sub.5 CO                        2-30    F      Cl     O    O   CH.sub.3                                                                           C.sub.6 H.sub.5 CH.sub.2                  2-31    F      Cl     O    O   CH.sub.3                                                                           CH.sub.3 OOCCH.sub.2                      2-32    F      Cl     O    O   CH.sub.3                                                                           CH.sub.3 SO.sub.2                         2-33    H      Cl     O    O   H    (CH.sub.3).sub.2 CH                       2-34    H      Cl     O    O   H    ClCH.sub.2 CH.sub.2                       2-35    F      Cl     O    O   H    CH.sub.3 OCH.sub.2                        2-36    H      Cl     O    O   H    CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2                                         .                                         2-37    H      Cl     O    O   H    CH.sub.3 SCH.sub.2                        2-38    H      Cl     O    O   H    CH.sub.2 CHCH.sub.2                       2-39    H      Cl     O    O   H    CH.sub.2 CClCH.sub.2                      2-40    H      Cl     O    O   H    CH CCH.sub.2                              2-41    H      Cl     O    O   H    CH CCH(CH.sub.3)                          2-42    H      Cl     O    O   H    cC.sub.5 H.sub.9                          2-43    H      Cl     O    O   H    CH.sub.3 CO                               2-44    H      Cl     O    O   H    CH.sub.3 NHCO                             2-45    H      Cl     O    O   H    C.sub.6 H.sub.5 CO                        2-46    H      Cl     O    O   M    C.sub.6 H.sub.5 CH.sub.2                  2-47    H      Cl     O    O   H    CH.sub.3 OOCCH.sub.2                      2-48    H      Cl     O    O   H    CH.sub.3 SO.sub.2                         2-49    H      Cl     O    O   CH.sub.3                                                                           (CH.sub.3).sub.2 CH                       2-50    H      Cl     O    O   CH.sub.3                                                                           ClCH.sub.2 CH.sub.2                       2-51    H      Cl     O    O   CH.sub.3                                                                           CH.sub.3 OCH.sub.2                        2-52    H      Cl     O    O   CH.sub.3                                                                           CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2     2-53    H      Cl     O    O   CH.sub.3                                                                           CH.sub.3 SCH.sub.2                        2-54    H      Cl     O    O   CH.sub.3                                                                           CH.sub.2 CHCH.sub.2                       2-55    H      Cl     O    O   CH.sub.3                                                                           CH.sub.2 CClCH.sub.2                      2-56    H      Cl     O    O   CH.sub.3                                                                           CH CCH.sub.2                              2-57    H      Cl     O    O   CH.sub.3                                                                           CH CCH(CH.sub.3)                          2-58    H      Cl     O    O   CH.sub.3                                                                           cC.sub.5 H.sub.9                          2-59    H      Cl     O    O   CH.sub.3                                                                           CH.sub.3 CO                               2-60    H      Cl     O    O   CH.sub.3                                                                           CH.sub.3 NHCO                             2-61    H      Cl     O    O   CH.sub.3                                                                           C.sub.6 H.sub.5 CO                        2-62    H      Cl     O    O   CH.sub.3                                                                           C.sub.6 H.sub.5 CH.sub.2                  2-63    H      Cl     O    O   CH.sub.3                                                                           CH.sub.3 OOCCH.sub.2                      2-64    H      Cl     O    O   CH.sub.3                                                                           CH.sub.3 SO.sub.2                         2-65    F      Cl     S    O   CH.sub.3                                                                           (CH.sub.3).sub.2 CH                       2-66    F      Br     O    O   CH.sub.3                                                                           (CH.sub.3).sub.2 CH                       2-67    F      F      O    O   CH.sub.3                                                                           (CH.sub.3).sub.2 CH                       2-68    Cl     Cl     O    O   CH.sub.3                                                                           (CH.sub.3).sub.2 CH                       ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                         ##STR9##                                                                     Compound                                                                      No.     X      Y      A.sup.1                                                                            A.sup.2                                                                           R.sup.1                                                                            R.sup.2                                   ______________________________________                                        3-1     F      Cl     O    O   H    (CH.sub.3).sub.2 CH                       3-2     F      Cl     O    O   H    ClCH.sub.2 CH.sub.2                       3-3     F      Cl     O    O   H    CH.sub.3 OCH.sub.2                        3-4     F      Cl     O    O   H    CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2     3-5     F      Cl     O    O   H    CH.sub.3 SCH.sub.2                        3-6     F      Cl     O    O   H    CH.sub.2 CHCH.sub.2                       3-7     F      Cl     O    O   H    CH.sub.2 CClCH.sub.2                      3-8     F      Cl     O    O   H    CH CCH.sub.2                              3-9     F      Cl     O    O   H    CH CCH(CH.sub.3)                          3-10    F      Cl     O    O   H    cC.sub.5 H.sub.9                          3-11    F      Cl     O    O   H    CH.sub.3 CO                               3-12    F      Cl     O    O   H    CH.sub.3 NHCO                             3-13    F      Cl     O    O   H    C.sub.6 H.sub.5 CO                        3-14    F      Cl     O    O   H    C.sub.6 H.sub.5 CH.sub.2                  3-15    F      Cl     O    O   H    CH.sub.3 OOCCH.sub.2                      3-16    F      Cl     O    O   H    CH.sub.3 SO.sub.2                         3-17    F      Cl     O    O   CH.sub.3                                                                           (CH.sub.3).sub.2 CH                       3-18    F      Cl     O    O   CH.sub.3                                                                           ClCH.sub.2 CH.sub.2                       3-19    F      Cl     O    O   CH.sub.3                                                                           CH.sub.3 OCH.sub.2                        3-20    F      Cl     O    O   CH.sub.3                                                                           CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2     3-21    F      Cl     O    O   CH.sub.3                                                                           CH.sub.3 SCH.sub.2                        3-22    F      Cl     O    O   CH.sub.3                                                                           CH.sub.2 CHCH.sub.2                       3-23    F      Cl     O    O   CH.sub.3                                                                           CH.sub.2 CClCH.sub.2                      3-24    F      Cl     O    O   CH.sub.3                                                                           CH CCH.sub.2                              3-25    F      Cl     O    O   CH.sub.3                                                                           CH CCH(CH.sub.3)                          3-26    F      Cl     O    O   CH.sub.3                                                                           cC.sub.5 H.sub.9                          3-27    F      Cl     O    O   CH.sub.3                                                                           CH.sub.3 CO                               3-28    F      Cl     O    O   CH.sub.3                                                                           CH.sub.3 NHCO                             3-29    F      Cl     O    O   CH.sub.3                                                                           C.sub.6 H.sub.5 CO                        3-30    F      Cl     O    O   CH.sub.3                                                                           C.sub.6 H.sub.5 CH.sub.2                  3-31    F      Cl     O    O   CH.sub.3                                                                           CH.sub.3 OOCCH.sub.2                      3-32    F      Cl     O    O   CH.sub.3                                                                           CH.sub.3 SO.sub.2                         3-33    H      Cl     O    O   H    (CH.sub.3).sub.2 CH                       3-34    H      Cl     O    O   H    ClCH.sub.2 CH.sub.2                       3-35    F      Cl     O    O   H    CH.sub.3 OCH.sub.2                        3-36    H      Cl     O    O   H    CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2     3-37    H      Cl     O    O   H    CH.sub.3 SCH.sub.2                        3-38    H      Cl     O    O   H    CH.sub.2 CHCH.sub.2                       3-39    H      Cl     O    O   H    CH.sub.2 CClCH.sub.2                      3-40    H      Cl     O    O   H    CH CCH.sub.2                              3-41    H      Cl     O    O   H    CH CCH(CH.sub.3)                          3-42    H      Cl     O    O   H    cC.sub.5 H.sub.9                          3-43    H      Cl     O    O   H    CH.sub.3 CO                               3-44    H      Cl     O    O   H    CH.sub.3 NHCO                             3-45    H      Cl     O    O   H    C.sub.6 H.sub.5 CO                        3-46    H      Cl     O    O   H    C.sub.6 H.sub.5 CH.sub.2                  3-47    H      Cl     O    O   H    CH.sub.3 OOCCH.sub.2                      3-48    H      Cl     O    O   H    CH.sub.3 SO.sub.2                         3-49    H      Cl     O    O   CH.sub.3                                                                           (CH.sub.3).sub.2 CH                       3-50    H      Cl     O    O   CH.sub.3                                                                           ClCH.sub.2 CH.sub.2                       3-51    H      Cl     O    O   CH.sub.3                                                                           CH.sub.3 OCH.sub.2                        3-52    H      Cl     O    O   CH.sub.3                                                                           CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2     3-53    H      Cl     O    O   CH.sub.3                                                                           CH.sub.3 SCH.sub.2                        3-54    H      Cl     O    O   CH.sub.3                                                                           CH.sub.2 CHCH.sub.2                       3-55    H      Cl     O    O   CH.sub.3                                                                           CH.sub.2 CClCH.sub.2                      3-56    H      Cl     O    O   CH.sub.3                                                                           CH CCH.sub.2                              3-57    H      Cl     O    O   CH.sub.3                                                                           CH CCH(CH.sub.3)                          3-58    H      Cl     O    O   CH.sub.3                                                                           cC.sub.5 H.sub.9                          3-59    H      Cl     O    O   CH.sub.3                                                                           CH.sub.3 CO                               3-60    H      Cl     O    O   CH.sub.3                                                                           CH.sub.3 NHCO                             3-61    H      Cl     O    O   CH.sub.3                                                                           C.sub.6 H.sub.5 CO                        3-62    H      Cl     O    O   CH.sub.3                                                                           C.sub.6 H.sub.5 CH.sub.2                  3-63    H      Cl     O    O   CH.sub.3                                                                           CH.sub.3 OOCCH.sub.2                      3-64    H      Cl     O    O   CH.sub.3                                                                           CH.sub.3 SO.sub.2                         3-65    F      Cl     S    O   CH.sub.3                                                                           (CH.sub.3).sub.2 CH                       3-66    F      Br     O    O   CH.sub.3                                                                           (CH.sub.3).sub.2 CH                       3-67    F      F      O    O   CH.sub.3                                                                           (CH.sub.3).sub.2 CH                       3-68    Cl     Cl     O    O   CH.sub.3                                                                           (CH.sub.3).sub.2 CH                       ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                         ##STR10##                                                                    Compound                                                                      No.     X      Y      R.sup.11                                                                             R.sup.1                                                                             R.sup.12                                   ______________________________________                                        4-1     F      Cl     (CH.sub.3).sub.3 C                                                                   H     (CH.sub.3).sub.2 CH                        4-2     F      Cl     (CH.sub.3).sub.3 C                                                                   H     ClCH.sub.2 CH.sub.2                        4-3     F      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.3 OCH.sub.2                         4-4     F      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2      4-5     F      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.3 SCH.sub.2                         4-6     F      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.2 CHCH.sub.2                        4-7     F      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.2 CClCH.sub.2                       4-8     F      Cl     (CH.sub.3).sub.3 C                                                                   H     CH CCH.sub.2                               4-9     F      Cl     (CH.sub.3).sub.3 C                                                                   H     CH CCH(CH.sub.3)                           4-10    F      Cl     (CH.sub.3).sub.3 C                                                                   H     cC.sub.5 H.sub.9                           4-11    F      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.3 CO                                4-12    F      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.3 NHCO                              4-13    F      Cl     (CH.sub.3).sub.3 C                                                                   H     C.sub.6 H.sub.5 CO                         4-14    F      Cl     (CH.sub.3).sub.3 C                                                                   H     C.sub.6 H.sub.5 CH.sub.2                   4-15    F      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.3 OOCCH.sub.2                       4-16    F      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.3 SO.sub.2                          4-17    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            (CH.sub.3).sub.2 CH                        4-18    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            ClCH.sub.2 CH.sub.2                        4-19    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.3 OCH.sub.2                         4-20    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2      4-21    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.3 SCH.sub.2                         4-22    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                        4-23    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.2 CClCH.sub.2                       4-24    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH CCH.sub.2                               4-25    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH CCH(CH.sub.3)                           4-26    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            cC.sub.5 H.sub.9                           4-27    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.3 CO                                4-28    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.3 NHCO                              4-29    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            C.sub.6 H.sub.5 CO                         4-30    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            C.sub.6 H.sub.5 CH.sub.2                   4-31    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.3 OOCCH.sub.2                       4-32    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.3 SO.sub.2                          4-33    H      Cl     (CH.sub.3).sub.3 C                                                                   H     (CH.sub.3).sub.2 CH                        4-34    H      Cl     (CH.sub.3).sub.3 C                                                                   H     ClCH.sub.2 CH.sub.2                        4-35    H      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.3 OCH.sub.2                         4-36    H      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2      4-37    H      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.3 SCH.sub.2                         4-38    H      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.2 CHCH.sub.2                        4-39    H      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.2 CClCH.sub.2                       4-40    H      Cl     (CH.sub.3).sub.3 C                                                                   H     CH CCH.sub.2                               4-41    H      Cl     (CH.sub.3).sub.3 C                                                                   H     CH CCH(CH.sub.3)                           4-42    H      Cl     (CH.sub.3).sub.3 C                                                                   H     cC.sub.5 H.sub.9                           4-43    H      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.3 CO                                4-44    H      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.3 NHCO                              4-45    H      Cl     (CH.sub.3).sub.3 C                                                                   H     C.sub.6 H.sub.5 CO                         4-46    H      Cl     (CH.sub.3).sub.3 C                                                                   H     C.sub.6 H.sub.5 CH.sub.2                   4-47    H      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.3 OOCCH.sub.2                       4-48    H      Cl     (CH.sub.3).sub.3 C                                                                   H     CH.sub.3 SO.sub.2                          4-49    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            (CH.sub.3).sub.2 CH                        4-50    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            ClCH.sub.2 CH.sub.2                        4-51    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.3 OCH.sub.2                         4-52    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2      4-53    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.3 SCH.sub.2                         4-54    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                        4-55    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.2 CClCH.sub.2                       4-56    H      Cl     (CH.sub.3).sub.3 CH                                                                  CH.sub.3                                                                            CH CCH.sub.2                               4-57    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH CCH(CH.sub.3)                           4-58    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            cC.sub.5 H.sub.9                           4-59    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.3 CO                                4-60    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.3 NHCO                              4-61    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            C.sub.6 H.sub.5 CO                         4-62    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            C.sub.6 H.sub.5 CH.sub.2                   4-63    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.3 OOCCH.sub.2                       4-64    H      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            CH.sub.3 SO.sub.2                          4-65    Cl     Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            (CH.sub.3).sub.2 CH                        4-66    F      Cl     CH.sub.3                                                                             CH.sub.3                                                                            (CH.sub.3).sub.2 CH                        4-67    F      Cl     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            (CH.sub.3).sub.2 CH                        4-68    F      Br     (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            (CH.sub.3).sub.2 CH                        4-69    F      F      (CH.sub.3).sub.3 C                                                                   CH.sub.3                                                                            (CH.sub.3).sub.2 CH                        ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                         ##STR11##                                                                    Compound                                                                      No.     X      Y      R.sup.12                                                                            R.sup.1                                                                             R.sup.2                                     ______________________________________                                        5-1     F      Cl     Cl    H     (CH.sub.3).sub.2 CH                         5-2     F      Cl     Cl    H     ClCH.sub.2 CH.sub.2                         5-3     F      Cl     Cl    H     CH.sub.3 OCH.sub.2                          5-4     F      Cl     Cl    H     CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2       5-5     F      Cl     Cl    H     CH.sub.3 SCH.sub.2                          5-6     F      Cl     Cl    H     CH.sub.2 CHCH.sub.2                         5-7     F      Cl     Cl    H     CH.sub.2 CClCH.sub.2                        5-8     F      Cl     Cl    H     CH CCH.sub.2                                5-9     F      Cl     Cl    H     CH CCH(CH.sub.3)                            5-10    F      Cl     Cl    H     cC.sub.5 H.sub.9                            5-11    F      Cl     Cl    H     CH.sub.3 CO                                 5-12    F      Cl     Cl    H     CH.sub.3 NHCO                               5-13    F      Cl     Cl    H     C.sub.6 H.sub.5 CO                          5-14    F      Cl     Cl    H     C.sub.6 H.sub.5 CH.sub.2                    5-15    F      Cl     Cl    H     CH.sub.3 OOCCH.sub.2                        5-16    F      Cl     Cl    H     CH.sub.3 SO.sub.2                           5-17    F      Cl     Cl    CH.sub.3                                                                            (CH.sub.3).sub.2 CH                         5-18    F      Cl     Cl    CH.sub.3                                                                            ClCH.sub.2 CH.sub.2                         5-19    F      Cl     Cl    CH.sub.3                                                                            CH.sub.3 OCH.sub.2                          5-20    F      Cl     Cl    CH.sub.3                                                                            CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2       5-21    F      Cl     Cl    CH.sub.3                                                                            CH.sub.3 SCH.sub.2                          5-22    F      Cl     Cl    CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                         5-23    F      Cl     Cl    CH.sub.3                                                                            CH.sub.2 CClCH.sub.2                        5-24    F      Cl     Cl    CH.sub.3                                                                            CH CCH.sub.2                                5-25    F      Cl     Cl    CH.sub.3                                                                            CH CCH(CH.sub.3)                            5-26    F      Cl     Cl    CH.sub.3                                                                            cC.sub.5 H.sub.9                            5-27    F      Cl     Cl    CH.sub.3                                                                            CH.sub.3 CO                                 5-28    F      Cl     Cl    CH.sub.3                                                                            CH.sub.3 NHCO                               5-29    F      Cl     Cl    CH.sub.3                                                                            C.sub.6 H.sub.5 CO                          5-30    F      Cl     Cl    CH.sub.3                                                                            C.sub.6 H.sub.5 CH.sub.2                    5-31    F      Cl     Cl    CH.sub.3                                                                            CH.sub.3 OOCCH.sub.2                        5-32    F      Cl     Cl    CH.sub.3                                                                            CH.sub.3 SO.sub.2                           5-33    H      Cl     Cl    H     (CH.sub.3).sub.2 CH                         5-34    H      Cl     Cl    H     ClCH.sub.2 CH.sub.2                         5-35    H      Cl     Cl    H     CH.sub.3 OCH.sub.2                          5-36    H      Cl     Cl    H     CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2       5-37    H      Cl     Cl    H     CH.sub.3 SCH.sub.2                          5-38    H      Cl     Cl    H     CH.sub.2 CHCH.sub.2                         5-39    H      Cl     Cl    H     CH.sub.2 CClCH.sub.2                        5-40    H      Cl     Cl    H     CH CCH.sub.2                                5-41    H      Cl     Cl    H     CH CCH(CH.sub.3)                            5-42    H      Cl     Cl    H     cC.sub.5 H.sub.9                            5-43    H      Cl     Cl    H     CH.sub.3 CO                                 5-44    H      Cl     Cl    H     CH.sub.3 NHCO                               5-45    H      Cl     Cl    H     C.sub.6 H.sub.5 CO                          5-46    H      Cl     Cl    H     C.sub.6 H.sub.5 CH.sub.2                    5-47    H      Cl     Cl    H     CH.sub.3 OOCCH.sub.2                        5-48    H      Cl     Cl    H     CH.sub.3 SO.sub.2                           5-49    H      Cl     Cl    CH.sub.3                                                                            (CH.sub.3).sub.2 CH                         5-50    H      Cl     Cl    CH.sub.3                                                                            ClCH.sub.2 CH.sub.2                         5-51    H      Cl     Cl    CH.sub.3                                                                            CH.sub.3 OCH.sub.2                          5-52    H      Cl     Cl    CH.sub.3                                                                            CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2       5-53    H      Cl     Cl    CH.sub.3                                                                            CH.sub.3 SCH.sub.2                          5-54    H      Cl     Cl    CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                         5-55    H      Cl     Cl    CH.sub.3                                                                            CH.sub.2 CClCH.sub.2                        5-56    H      Cl     Cl    CH.sub.3                                          CH CCH.sub.2                                                                  5-57    H      Cl     Cl    CH.sub.3                                                                            CH CCH(CH.sub.3)                            5-58    H      Cl     Cl    CH.sub.3                                                                            cC.sub.5 H.sub.9                            5-59    H      Cl     Cl    CH.sub.3                                                                            CH.sub.3 CO                                 5-60    H      Cl     Cl    CH.sub.3                                                                            CH.sub.3 NHCO                               5-61    H      Cl     Cl    CH.sub.3                                                                            C.sub.6 H.sub.5 CO                          5-62    H      Cl     Cl    CH.sub.3                                                                            C.sub.6 H.sub.5 CH.sub.2                    5-63    H      Cl     Cl    CH.sub.3                                                                            CH.sub.3 OOCCH.sub.2                        5-64    H      Cl     Cl    CH.sub.3                                                                            CH.sub.3 SO.sub.2                           5-65    F      Br     Cl    H     (CH.sub.3).sub.2 CH                         5-66    F      F      Cl    H     (CH.sub.3).sub.2 CH                         5-67    Cl     Cl     Cl    H     (CH.sub.3).sub.2 CH                         5-68    F      Cl     OCH.sub.3                                                                           H     (CH.sub.3).sub.2 CH                         5-69    F      Cl     CH.sub.3                                                                            H     (CH.sub.3).sub.2 CH                         ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                         ##STR12##                                                                    (compound wherein Q is Q-6.)                                                  Compound                                                                      No.        X      Y      R.sup.1                                                                             R.sup.2                                        ______________________________________                                        6-1        F      Cl     H     (CH.sub.3).sub.2 CH                            6-2        F      Cl     H     ClCH.sub.2 CH.sub.2                            6-3        F      Cl     H     CH.sub.3 OCH.sub.2                             6-4        F      Cl     H     CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          6-5        F      Cl     H     CH.sub.3 SCH.sub.2                             6-6        F      Cl     H     CH.sub.2CHCH.sub.2                             6-7        F      Cl     H     CH.sub.2CClCH.sub.2                            6-8        F      Cl     H     CHCCH.sub.2                                    6-9        F      Cl     H     CHCCH(CH.sub.3)                                6-10       F      Cl     H     cC.sub.5 H.sub.9                               6-11       F      Cl     H     CH.sub.3 CO                                    6-12       F      Cl     H     CH.sub.3 NHCO                                  6-13       F      Cl     H     C.sub.6 H.sub.5 CO                             6-14       F      Cl     H     C.sub.6 H.sub.5 CH.sub.2                       6-15       F      Cl     H     CH.sub.3 OOCCH.sub.2                           6-16       F      Cl     H     CH.sub.3 SO.sub.2                              6-17       F      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 CH                            6-18       F      Cl     CH.sub.3                                                                            ClCH.sub.2 CH.sub.2                            6-19       F      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2                             6-20       F      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          6-21       F      Cl     CH.sub.3                                                                            CH.sub.3 SCH.sub.2                             6-22       F      Cl     CH.sub.3                                                                            CH.sub.2CHCH.sub.2                             6-23       F      Cl     CH.sub.3                                                                            CH.sub.2CClCH.sub.2                            6-24       F      Cl     CH.sub.3                                                                            CHCCH.sub.2                                    6-25       F      Cl     CH.sub.3                                                                            CHCCH(CH.sub.3)                                6-26       F      Cl     CH.sub.3                                                                            cC.sub.5 H.sub.9                               6-27       F      Cl     CH.sub.3                                                                            CH.sub.3 CO                                    6-28       F      Cl     CH.sub.3                                                                            CH.sub.3 NHCO                                  6-29       F      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CO                             6-30       F      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CH.sub.2                       6-31       F      Cl     CH.sub.3                                                                            CH.sub.3 OOCCH.sub.2                           6-32       F      Cl     CH.sub.3                                                                            CH.sub.3 SO.sub.2                              6-33       H      Cl     H     (CH.sub.3).sub.2 CH                            6-34       H      Cl     H     ClCH.sub.2 CH.sub.2                            6-35       H      Cl     H     CH.sub.3 OCH.sub.2                             6-36       H      Cl     H     CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          6-37       H      Cl     H     CH.sub.3 SCH.sub.2                             6-38       H      Cl     H     CH.sub.2CHCH.sub.2                             6-39       H      Cl     H     CH.sub.2CClCH.sub.2                            6-40       H      Cl     H     CHCCH.sub.2                                    6-41       H      Cl     H     CHCCH(CH.sub.3)                                6-42       H      Cl     H     cC.sub.5 H.sub.9                               6-43       H      Cl     H     CH.sub.3 CO                                    6-44       H      Cl     H     CH.sub.3 NHCO                                  6-45       H      Cl     H     C.sub.6 H.sub.5 CO                             6-46       H      Cl     H     C.sub.6 H.sub.5 CH.sub.2                       6-47       H      Cl     H     CH.sub.3 OOCCH.sub.2                           6-48       H      Cl     H     CH.sub.3 SO.sub.2                              6-49       H      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 CH                            6-50       H      Cl     CH.sub.3                                                                            ClCH.sub.2 CH.sub.2                            6-51       H      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2                             6-52       H      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          6-53       H      Cl     CH.sub.3                                                                            CH.sub.3 SCH.sub.2                             6-54       H      Cl     CH.sub.3                                                                            CH.sub.2CHCH.sub.2                             6-55       H      Cl     CH.sub.3                                                                            CH.sub.2CClCH.sub.2                            6-56       H      Cl     CH.sub.3                                                                            CHCCH.sub.2                                    6-57       H      Cl     CH.sub.3                                                                            CHCCH(CH.sub.3)                                6-58       H      Cl     CH.sub.3                                                                            cC.sub.5 H.sub.9                               6-59       H      Cl     CH.sub.3                                                                            CH.sub.3 CO                                    6-60       H      Cl     CH.sub.3                                                                            CH.sub.3 NHCO                                  6-61       H      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CO                             6-62       H      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CH.sub.2                       6-63       H      Cl     CH.sub.3                                                                            CH.sub.3 OOCCH.sub.2                           6-64       H      Cl     CH.sub.3                                                                            CH.sub.3 SO.sub.2                              6-65       F      Br     H     (CH.sub.3).sub.2 CH                            6-66       F      F      H     (CH.sub.3).sub.2 CH                            6-67       Cl     Cl     H     (CH.sub.3).sub.2 CH                            ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                         ##STR13##                                                                    (compound wherein Q is Q-7.)                                                  Compound                                                                      No.        X      Y      R.sup.1                                                                             R.sup.2                                        ______________________________________                                        7-1        F      Cl     H     (CH.sub.3).sub.2 CH                            7-2        F      Cl     H     ClCH.sub.2 CH.sub.2                            7-3        F      Cl     H     CH.sub.3 OCH.sub.2                             7-4        F      Cl     H     CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          7-5        F      Cl     H     CH.sub.3 SCH.sub.2                             7-6        F      Cl     H     CH.sub.2CHCH.sub.2                             7-7        F      Cl     H     CH.sub.2CClCH.sub.2                            7-8        F      Cl     H     CHCCH.sub.2                                    7-9        F      Cl     H     CHCCH(CH.sub.3)                                7-10       F      Cl     H     cC.sub.5 H.sub.9                               7-11       F      Cl     H     CH.sub.3 CO                                    7-12       F      Cl     H     CH.sub.3 NHCO                                  7-13       F      Cl     H     C.sub.6 H.sub.5 CO                             7-14       F      Cl     H     C.sub.6 H.sub.5 CH.sub.2                       7-15       F      Cl     H     CH.sub.3 OOCCH.sub.2                           7-16       F      Cl     H     CH.sub.3 SO.sub.2                              7-17       F      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 CH                            7-18       F      Cl     CH.sub.3                                                                            ClCH.sub.2 CH.sub.2                            7-19       F      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2                             7-20       F      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          7-21       F      Cl     CH.sub.3                                                                            CH.sub.3 SCH.sub.2                             7-22       F      Cl     CH.sub.3                                                                            CH.sub.2CHCH.sub.2                             7-23       F      Cl     CH.sub.3                                                                            CH.sub.2CClCH.sub.2                            7-24       F      Cl     CH.sub.3                                                                            CHCCH.sub.2                                    7-25       F      Cl     CH.sub.3                                                                            CHCCH(CH.sub.3)                                7-26       F      Cl     CH.sub.3                                                                            cC.sub.5 H.sub.9                               7-27       F      Cl     CH.sub.3                                                                            CH.sub.3 CO                                    7-28       F      Cl     CH.sub.3                                                                            CH.sub.3 NHCO                                  7-29       F      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CO                             7-30       F      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CH.sub.2                       7-31       F      Cl     CH.sub.3                                                                            CH.sub.3 OOCCH.sub.2                           7-32       F      Cl     CH.sub.3                                                                            CH.sub.3 SO.sub.2                              7-33       H      Cl     H     (CH.sub.3).sub.2 CH                            7-34       H      Cl     H     ClCH.sub.2 CH.sub.2                            7-35       H      Cl     H     CH.sub.3 OCH.sub.2                             7-36       H      Cl     H     CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          7-37       H      Cl     H     CH.sub.3 SCH.sub.2                             7-38       H      Cl     H     CH.sub.2CHCH.sub.2                             7-39       H      Cl     H     CH.sub.2CClCH.sub.2                            7-40       H      Cl     H     CHCCH.sub.2                                    7-41       H      Cl     H     CHCCH(CH.sub.3)                                7-42       H      Cl     H     cC.sub.5 H.sub.9                               7-43       H      Cl     H     CH.sub.3 CO                                    7-44       H      Cl     H     CH.sub.3 NHCO                                  7-45       H      Cl     H     C.sub.6 H.sub.5 CO                             7-46       H      Cl     H     C.sub.6 H.sub.5 CH.sub.2                       7-47       H      Cl     H     CH.sub.3 OOCCH.sub.2                           7-48       H      Cl     H     CH.sub.3 SO.sub.2                              7-49       H      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 CH                            7-50       H      Cl     CH.sub.3                                                                            ClCH.sub.2 CH.sub.2                            7-51       H      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2                             7-52       H      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          7-53       H      Cl     CH.sub.3                                                                            CH.sub.3 SCH.sub.2                             7-54       H      Cl     CH.sub.3                                                                            CH.sub.2CHCH.sub.2                             7-55       H      Cl     CH.sub.3                                                                            CH.sub.2CClCH.sub.2                            7-56       H      Cl     CH.sub.3                                                                            CHCCH.sub.2                                    7-57       H      Cl     CH.sub.3                                                                            CHCCH(CH.sub.3)                                7-58       H      Cl     CH.sub.3                                                                            cC.sub.5 H.sub.9                               7-59       H      Cl     CH.sub.3                                                                            CH.sub.3 CO                                    7-60       H      Cl     CH.sub.3                                                                            CH.sub.3 NHCO                                  7-61       H      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CO                             7-62       H      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CH.sub.2                       7-63       H      Cl     CH.sub.3                                                                            CH.sub.3 OOCCH.sub.2                           7-64       H      Cl     CH.sub.3                                                                            CH.sub.3 SO.sub.2                              7-65       F      Br     H     (CH.sub.3).sub.2 CH                            7-66       F      F      H     (CH.sub.3).sub.2 CH                            7-67       Cl     Cl     H     (CH.sub.3).sub.2 CH                            ______________________________________                                    

                                      TABLE 8                                     __________________________________________________________________________     ##STR14##                                                                    (compound wherein Q is Q-8.)                                                  Compound                                                                      No.    X  Y  A.sup.1                                                                          R.sup.13                                                                          R.sup.14                                                                           R.sup.15                                                                          R.sup.1                                                                           R.sup.2                                      __________________________________________________________________________    8-1    F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3                                     8-2    F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.2 H.sub.5                              8-3    F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.2 CH                          8-4    F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.3 C                           8-5    F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   ClCH.sub.2 CH.sub.2                          8-6    F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 OCH.sub.2                           8-7    F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.2 H.sub.5 OCH.sub.2                    8-8    F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 OCH.sub.2 CH.sub.2                  8-9    F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2        8-10   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 SCH.sub.2                           8-11   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.2CHCH.sub.2                           8-12   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.2CHCH.sub.2 CH.sub.2                  8-13   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3CHCHCH.sub.2                         8-14   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.2CClCH.sub.2                          8-15   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CCl.sub.2CHCH.sub.2                          8-16   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CHCCH.sub.2                                  8-17   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CHCCH(CH.sub.3)                              8-18   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   BrCCCH.sub.2                                 8-19   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   cC.sub.5 H.sub.9                             8-20   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   cC.sub.6 H.sub.11                            8-21   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 CO                                  8-22   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.2 H.sub.5 CO                           8-23   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.2 CHCO                        8-24   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.3 CCO                         8-25   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.6 H.sub.5 CO                           8-26   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   p-CH.sub.3 OC.sub.6 H.sub.4 CO               8-27   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   p-CH.sub.3 C.sub.6 H.sub.5 CO                8-28   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   ClCH.sub.2 CO                                8-29   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 NHCO                                8-30   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.2 NCO                         8-31   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (C.sub.2 H.sub.5).sub.2 NCO                  8-32   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.6 H.sub.5 CH.sub.2                     8-33   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   p-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2         8-34   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   p-ClC.sub.6 H.sub.4 CH.sub.2                 8-35   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.6 H.sub.5 CH.sub.2 CH.sub.2            8-36   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 OOCCH.sub.2                         8-37   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.2 H.sub.5 OOCCH.sub.2                  8-38   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.2 CHOOCCH.sub.2               8-39   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   .sup.n C.sub.4 H.sub.9 OOCCH.sub.2           8-40   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   .sup.n C.sub.5 H.sub.11 OOCCH.sub.2          8-41   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 OOCCH(CH.sub.3)                     8-42   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.2 H.sub.5 OOCCH(CH.sub.3)              8-43   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   cC.sub.5 H.sub.9 OOCCH.sub.2                 8-44   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   cC.sub.6 H.sub.11 OOCCH.sub.2                8-45   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 SO.sub.2                            8-46   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.2 H.sub.5 SO.sub.2                     8-47   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.2 CHSO.sub.2                  8-48   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   ClCH.sub.2 SO.sub.2                          8-49   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.6 H.sub.5 SO.sub.2                     8-50   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   p-CH.sub.3 C.sub.6 H.sub.4 SO.sub.2          8-51   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                     8-52   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.2 H.sub.5                              8-53   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (CH.sub.3).sub.2 CH                          8-54   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (CH.sub.3).sub.3 C                           8-55   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          ClCH.sub.2 CH.sub.2                          8-56   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 OCH.sub.2                           8-57   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.2 H.sub.5 OCH.sub.2                    8-58   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 OCH.sub.2 CH.sub.2                  8-59   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2        8-60   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 SCH.sub.2                           8-61   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.2CHCH.sub.2                           8-62   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.2CHCH.sub.2 CH.sub.2                  8-63   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3CHCHCH.sub.2                         8-64   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.2CClCH.sub.2                          8-65   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CCl.sub.2CHCH.sub.2                          8-66   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CHCCH.sub.2                                  8-67   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CHCCH(CH.sub.3)                              8-68   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          BrCCCH.sub.2                                 8-69   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          cC.sub.5 H.sub.9                             8-70   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          cC.sub.6 H.sub.11                            8-71   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 CO                                  8-72   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.2 H.sub.5 CO                           8-73   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (CH.sub.3).sub.2 CHCO                        8-74   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (CH.sub.3).sub.3 CCO                         8-75   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.6 H.sub.5 CO                           8-76   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          p-CH.sub.3 OC.sub.6 H.sub.4 CO               8-77   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          p-CH.sub.3 C.sub.6 H.sub.5 CO                8-78   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          ClCH.sub.2 CO                                8-79   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 NHCO                                8-80   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (CH.sub.3).sub.2 NCO                         8-81   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (C.sub.2 H.sub.5).sub.2 NCO                  8-82   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.6 H.sub.5 CH.sub.2                     8-83   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          p-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2         8-84   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          p-ClC.sub.6 H.sub.4 CH.sub.2                 8-85   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.6 H.sub.5 CH.sub.2 CH.sub.2            8-86   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 OOCCH.sub.2                         8-87   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.2 H.sub.5 OOCCH.sub.2                  8-88   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (CH.sub.3).sub.2 CHOOCCH.sub.2               8-89   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          .sup.n C.sub.4 H.sub.9 OOCCH.sub.2           8-90   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          .sup.n C.sub.5 H.sub.11 OOCCH.sub.2          8-91   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 OOCCH(CH.sub.3)                     8-92   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.2 H.sub.5 OOCCH(CH.sub.3)              8-93   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          cC.sub.5 H.sub.9 OOCCH.sub.2                 8-94   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          cC.sub.6 H.sub.11 OOCCH.sub.2                8-95   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 SO.sub.2                            8-96   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.2 H.sub.5 SO.sub.2                     8-97   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (CH.sub.3).sub.2 CHSO.sub.2                  8-98   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          ClCH.sub.2 SO.sub.2                          8-99   F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.6 H.sub.5 SO.sub.2                     8-100  F  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          p-CH.sub.3 C.sub.6 H.sub.4 SO.sub.2          8-101  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3                                     8-102  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.2 H.sub.5                              8-103  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.2 CH                          8-104  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.3 C                           8-105  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   ClCH.sub.2 CH.sub.2                          8-106  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 OCH.sub.2                           8-107  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.2 H.sub.5 OCH.sub.2                    8-108  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 OCH.sub.2 CH.sub.2                  8-109  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2        8-110  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 SCH.sub.2                           8-111  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.2CHCH.sub.2                           8-112  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.2CHCH.sub.2 CH.sub.2                  8-113  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3CHCHCH.sub.2                         8-114  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.2CClCH.sub.2                          8-115  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CCl.sub.2CHCH.sub.2                          8-116  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CHCCH.sub.2                                  8-117  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CHCCH(CH.sub.3)                              8-118  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   BrCCCH.sub.2                                 8-119  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   cC.sub.5 H.sub.9                             8-120  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   cC.sub.6 H.sub.11                            8-121  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 CO                                  8-122  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.2 H.sub.5 CO                           8-123  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.2 CHCO                        8-124  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.3 CCO                         8-125  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.6 H.sub.5 CO                           8-126  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   p-CH.sub.3 OC.sub.6 H.sub.4 CO               8-127  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   p-CH.sub.3 C.sub.6 H.sub.5 CO                8-128  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   ClCH.sub.2 CO                                8-129  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 NHCO                                8-130  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.2 NCO                         8-131  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (C.sub.2 H.sub.5).sub.2 NCO                  8-132  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.6 H.sub.5 CH.sub.2                     8-133  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   p-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2         8-134  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   p-ClC.sub.6 H.sub.4 CH.sub.2                 8-135  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.6 H.sub.5 CH.sub.2 CH.sub.2            8-136  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 OOCCH.sub.2                         8-137  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.2 H.sub.5 OOCCH.sub.2                  8-138  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.2 CHOOCCH.sub.2               8-139  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   .sup.n C.sub.4 H.sub.9 OOCCH.sub.2           8-140  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   .sup.n C.sub.5 H.sub.11 OOCCH.sub.2          8-141  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 OOCCH(CH.sub.3)                     8-142  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.2 H.sub.5 OOCCH(CH.sub.3)              8-143  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   cC.sub.5 H.sub.9 OOCCH.sub.2                 8-144  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   cC.sub.6 H.sub.11 OOCCH.sub.2                8-145  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CH.sub.3 SO.sub.2                            8-146  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.2 H.sub.5 SO.sub.2                     8-147  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.2 CHSO.sub.2                  8-148  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   ClCH.sub.2 SO.sub.2                          8-149  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   C.sub.6 H.sub.5 SO.sub.2                     8-150  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   p-CH.sub.3 C.sub.6 H.sub.4 SO.sub.2          8-151  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                     8-152  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.2 H.sub.5                              8-153  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (CH.sub.3).sub.2 CH                          8-154  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (CH.sub.3).sub.3 C                           8-155  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          ClCH.sub.2 CH.sub.2                          8-156  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 OCH.sub.2                           8-157  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.2 H.sub.5 OCH.sub.2                    8-158  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 OCH.sub.2 CH.sub.2                  8-159  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2        8-160  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 SCH.sub.2                           8-161  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.2CHCH.sub.2                           8-162  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.2CHCH.sub.2 CH.sub.2                  8-163  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3CHCHCH.sub.2                         8-164  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.2CClCH.sub.2                          8-165  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CCl.sub.2CHCH.sub.2                          8-166  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CHCCH.sub.2                                  8-167  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CHCCH(CH.sub.3)                              8-168  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          BrCCCH.sub.2                                 8-169  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          cC.sub.5 H.sub.9                             8-170  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          cC.sub.6 H.sub.11                            8-171  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 CO                                  8-172  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.2 H.sub.5 CO                           8-173  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (CH.sub.3).sub.2 CHCO                        8-174  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (CH.sub.3).sub.3 CCO                         8-175  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.6 H.sub.5 CO                           8-176  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          p-CH.sub.3 OC.sub.6 H.sub.4 CO               8-177  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          p-CH.sub.3 C.sub.6 H.sub.5 CO                8-178  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          ClCH.sub.2 CO                                8-179  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 NHCO                                8-180  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (CH.sub.3).sub.2 NCO                         8-181  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (C.sub.2 H.sub.5).sub.2 NCO                  8-182  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.6 H.sub.5 CH.sub.2                     8-183  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          p-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2         8-184  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          p-ClC.sub.6 H.sub.4 CH.sub.2                 8-185  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.6 H.sub.5 CH.sub.2 CH.sub.2            8-186  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 OOCCH.sub.2                         8-187  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.2 H.sub.5 OOCCH.sub.2                  8-188  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (CH.sub.3).sub.2 CHOOCCH.sub.2               8-189  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          .sup.n C.sub.4 H.sub.9 OOCCH.sub.2           8-190  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          .sup.n C.sub.5 H.sub.11 OOCCH.sub.2          8-191  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 OOCCH(CH.sub.3)                     8-192  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.2 H.sub.5 OOCCH(CH.sub.3)              8-193  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          cC.sub.5 H.sub.9 OOCCH.sub.2                 8-194  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          cC.sub.6 H.sub.11 OOCCH.sub.2                8-195  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 SO.sub.2                            8-196  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.2 H.sub.5 SO.sub.2                     8-197  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          (CH.sub.3).sub.2 CHSO.sub.2                  8-198  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          ClCH.sub.2 SO.sub.2                          8-199  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          C.sub.6 H.sub.5 SO.sub.2                     8-200  H  Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          p-CH.sub.3 C.sub.6 H.sub.4 SO.sub.2          8-201  F  Br O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   (CH.sub.3).sub.2 CH                          8-202  F  F  O  H   CF.sub.3                                                                           CH.sub.3                                                                          H   CHCCH.sub.2                                  8-203  Cl Cl O  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CHCCH(CH.sub.3)                              8-204  F  Cl S  H   CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 CO                                  8-205  F  Cl O  H   CF.sub.3                                                                           NH.sub.2                                                                          CH.sub.3                                                                          C.sub.6 H.sub.5 CO                           8-206  F  Cl S  H   CF.sub.3                                                                           NH.sub.2                                                                          H   CH.sub.3 OCH.sub.2                           8-207  F  Cl O  H   CF.sub.3 CF.sub.2                                                                  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.2CHCH.sub.2                           8-208  F  Cl O  Cl  CF.sub.3                                                                           CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3 OOCCH.sub.2                         __________________________________________________________________________

                                      TABLE 9                                     __________________________________________________________________________     ##STR15##                                                                    (compound wherein Q is Q-9.)                                                  Compound                                                                      No.   X  Y  B  R.sup.15                                                                          R.sup.17                                                                         m  R.sup.1                                                                           R.sup.2                                          __________________________________________________________________________    9-1   F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   (CH.sub.3).sub.2 CH                              9-2   F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   ClCH.sub.2 CH.sub.2                              9-3   F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.3 OCH.sub.2                               9-4   F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2            9-5   F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.3 SCH.sub.2                               9-6   F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.2CHCH.sub.2                               9-7   F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.2CClCH.sub.2                              9-8   F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CHCCH.sub.2                                      9-9   F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CHCCH(CH.sub.3)                                  9-10  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   cC.sub.5 H.sub.9                                 9-11  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.3 CO                                      9-12  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.3 NHCO                                    9-13  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   C.sub.6 H.sub.5 CO                               9-14  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   C.sub.6 H.sub.5 CH.sub.2                         9-15  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.3 OOCCH.sub.2                             9-16  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.3 SO.sub.2                                9-17  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          (CH.sub.3).sub.2 CH                              9-18  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          ClCH.sub.2 CH.sub.2                              9-19  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.3 OCH.sub.2                               9-20  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2            9-21  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.3 SCH.sub.2                               9-22  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.2CHCH.sub.2                               9-23  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.2CClCH.sub.2                              9-24  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CHCCH.sub.2                                      9-25  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CHCCH(CH.sub.3)                                  9-26  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          cC.sub.5 H.sub.9                                 9-27  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.3 CO                                      9-28  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.3 NHCO                                    9-29  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          C.sub.6 H.sub.5 CO                               9-30  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          C.sub.6 H.sub.5 CH.sub.2                         9-31  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.3 OOCCH.sub.2                             9-32  F  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.3 SO.sub.2                                9-33  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   (CH.sub.3).sub.2 CH                              9-34  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   ClCH.sub.2 CH.sub.2                              9-35  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.3 OCH.sub.2                               9-36  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2            9-37  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.3 SCH.sub.2                               9-38  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.2CHCH.sub.2                               9-39  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.2CClCH.sub.2                              9-40  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CHCCH.sub.2                                      9-41  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CHCCH(CH.sub.3)                                  9-42  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   cC.sub.5 H.sub.9                                 9-43  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.3 CO                                      9-44  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.3 NHCO                                    9-45  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   C.sub.6 H.sub.5 CO                               9-46  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   C.sub.6 H.sub.5 CH.sub.2                         9-47  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.3 OOCCH.sub.2                             9-48  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  H   CH.sub.3 SO.sub.2                                9-49  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          (CH.sub.3).sub.2 CH                              9-50  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          ClCH.sub.2 CH.sub.2                              9-51  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.3 OCH.sub.2                               9-52  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2            9-53  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.3 SCH.sub.2                               9-54  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.2CHCH.sub.2                               9-55  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.2CClCH.sub.2                              9-56  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CHCCH.sub.2                                      9-57  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CHCCH(CH.sub.3)                                  9-58  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          cC.sub.5 H.sub.9                                 9-59  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.3 CO                                      9-60  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.3 NHCO                                    9-61  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          C.sub.6 H.sub.5 CO                               9-62  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          C.sub.6 H.sub.5 CH.sub.2                         9-63  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.3 OOCCH.sub.2                             9-64  H  Cl CH.sub.2                                                                         CH.sub.3                                                                          CH.sub.3                                                                         1  CH.sub.3                                                                          CH.sub.3 SO.sub.2                                __________________________________________________________________________

                  TABLE 10                                                        ______________________________________                                         ##STR16##                                                                    (compound wherein Q is Q-10.)                                                 Compound                                                                      No.     X      Y      A.sup.1                                                                            m    R.sup.1                                                                            R.sup.2                                  ______________________________________                                        10-1    F      Cl     O    2    H    (CH.sub.3).sub.2 CH                      10-2    F      Cl     O    2    H    ClCH.sub.2 CH.sub.2                      10-3    F      Cl     O    2    H    CH.sub.3 OCH.sub.2                       10-4    F      Cl     O    2    H    CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2    10-5    F      Cl     O    2    H    CH.sub.3 SCH.sub.2                       10-6    F      Cl     O    2    H    CH.sub.2CHCH.sub.2                       10-7    F      Cl     O    2    H    CH.sub.2CClCH.sub.2                      10-8    F      Cl     O    2    H    CHCCH.sub.2                              10-9    F      Cl     O    2    H    CHCCH(CH.sub.3)                          10-10   F      Cl     O    2    H    cC.sub.5 H.sub.9                         10-11   F      Cl     O    2    H    CH.sub.3 CO                              10-12   F      Cl     O    2    H    CH.sub.3 NHCO                            10-13   F      Cl     O    2    H    C.sub.6 H.sub.5 CO                       10-14   F      Cl     O    2    H    C.sub.6 H.sub.5 CH.sub.2                 10-15   F      Cl     O    2    H    CH.sub.3 OOCCH.sub.2                     10-16   F      Cl     O    2    H    CH.sub.3 SO.sub.2                        10-17   F      Cl     O    2    CH.sub.3                                                                           (CH.sub.3).sub.2 CH                      10-18   F      Cl     O    2    CH.sub.3                                                                           ClCH.sub.2 CH.sub.2                      10-19   F      Cl     O    2    CH.sub.3                                                                           CH.sub.3 OCH.sub.2                       10-20   F      Cl     O    2    CH.sub.3                                                                           CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2    10-21   F      Cl     O    2    CH.sub.3                                                                           CH.sub.3 SCH.sub.2                       10-22   F      Cl     O    2    CH.sub.3                                                                           CH.sub.2CHCH.sub.2                       10-23   F      Cl     O    2    CH.sub.3                                                                           CH.sub.2CClCH.sub.2                      10-24   F      Cl     O    2    CH.sub.3                                                                           CHCCH.sub.2                              10-25   F      Cl     O    2    CH.sub.3                                                                           CHCCH(CH.sub.3)                          10-26   F      Cl     O    2    CH.sub.3                                                                           cC.sub.5 H.sub.9                         10-27   F      Cl     O    2    CH.sub.3                                                                           CH.sub.3 CO                              10-28   F      Cl     O    2    CH.sub.3                                                                           CH.sub.3 NHCO                            10-29   F      Cl     O    2    CH.sub.3                                                                           C.sub.6 H.sub.5 CO                       10-30   F      Cl     O    2    CH.sub.3                                                                           C.sub.6 H.sub.5 CH.sub.2                 10-31   F      Cl     O    2    CH.sub.3                                                                           CH.sub.3 OOCCH.sub.2                     10-32   F      Cl     O    2    CH.sub.3                                                                           CH.sub.3 SO.sub.2                        10-33   H      Cl     O    2    H    (CH.sub.3).sub.2 CH                      10-34   H      Cl     O    2    H    ClCH.sub.2 CH.sub.2                      10-35   F      Cl     O    2    H    CH.sub.3 OCH.sub.2                       10-36   H      Cl     O    2    H    CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2    10-37   H      Cl     O    2    H    CH.sub.3 SCH.sub.2                       10-38   H      Cl     O    2    H    CH.sub.2CHCH.sub.2                       10-39   H      Cl     O    2    H    CH.sub.2CClCH.sub.2                      10-40   H      Cl     O    2    H    CHCCH.sub.2                              10-41   H      Cl     O    2    H    CHCCH(CH.sub.3)                          10-42   H      Cl     O    2    H    cC.sub.5 H.sub.9                         10-43   H      Cl     O    2    H    CH.sub.3 CO                              10-44   H      Cl     O    2    H    CH.sub.3 NHCO                            10-45   H      Cl     O    2    H    C.sub.6 H.sub.5 CO                       10-46   H      Cl     O    2    H    C.sub.6 H.sub.5 CH.sub.2                 10-47   H      Cl     O    2    H    CH.sub.3 OOCCH.sub.2                     10-48   H      Cl     O    2    H    CH.sub.3 SO.sub.2                        10-49   H      Cl     O    2    CH.sub.3                                                                           (CH.sub.3).sub.2 CH                      10-50   H      Cl     O    2    CH.sub.3                                                                           ClCH.sub.2 CH.sub.2                      10-51   H      Cl     O    2    CH.sub.3                                                                           CH.sub.3 OCH.sub.2                       10-52   H      Cl     O    2    CH.sub.3                                                                           CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2    10-53   H      Cl     O    2    CH.sub.3                                                                           CH.sub.3 SCH.sub.2                       10-54   H      Cl     O    2    CH.sub.3                                                                           CH.sub.2CHCH.sub.2                       10-55   H      Cl     O    2    CH.sub.3                                                                           CH.sub.2CClCH.sub.2                      10-56   H      Cl     O    2    CH.sub.3                                                                           CHCCH.sub.2                              10-57   H      Cl     O    2    CH.sub.3                                                                           CHCCH(CH.sub.3)                          10-58   H      Cl     O    2    CH.sub.3                                                                           cC.sub.5 H.sub.9                         10-59   H      Cl     O    2    CH.sub.3                                                                           CH.sub.3 CO                              10-60   H      Cl     O    2    CH.sub.3                                                                           CH.sub.3 NHCO                            10-61   H      Cl     O    2    CH.sub.3                                                                           C.sub.6 H.sub.5 CO                       10-62   H      Cl     O    2    CH.sub.3                                                                           C.sub.6 H.sub.5 CH.sub.2                 10-63   H      Cl     O    2    CH.sub.3                                                                           CH.sub.3 OOCCH.sub.2                     10-64   H      Cl     O    2    CH.sub.3                                                                           CH.sub.3 SO.sub.2                        10-65   F      Br     O    2    CH.sub.3                                                                           (CH.sub.3).sub.2 CH                      10-66   F      F      O    2    CH.sub.3                                                                           (CH.sub.3).sub.2 CH                      10-67   Cl     Cl     O    2    CH.sub.3                                                                           (CH.sub.3).sub.2 CH                      10-68   F      Cl     O    1    CH.sub.3                                                                           (CH.sub.3).sub.2 CH                      ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                         ##STR17##                                                                    Compound                                                                      No.        X      Y      R.sup.1                                                                             R.sup.2                                        ______________________________________                                        11-1       F      Cl     H     (CH.sub.3).sub.2 CH                            11-2       F      Cl     H     ClCH.sub.2 CH.sub.2                            11-3       F      Cl     H     CH.sub.3 OCH.sub.2                             11-4       F      Cl     H     CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          11-5       F      Cl     H     CH.sub.3 SCH.sub.2                             11-6       F      Cl     H     CH.sub.2CHCH.sub.2                             11-7       F      Cl     H     CH.sub.2CClCH.sub.2                            11-8       F      Cl     H     CHCCH.sub.2                                    11-9       F      Cl     H     CHCCH(CH.sub.3)                                11-10      F      Cl     H     cC.sub.5 H.sub.9                               11-11      F      Cl     H     CH.sub.3 CO                                    11-12      F      Cl     H     CH.sub.3 NHCO                                  11-13      F      Cl     H     C.sub.6 H.sub.5 CO                             11-14      F      Cl     H     C.sub.6 H.sub.5 CH.sub.2                       11-15      F      Cl     H     CH.sub.3 OOCCH.sub.2                           11-16      F      Cl     H     CH.sub.3 SO.sub.2                              11-17      F      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 CH                            11-18      F      Cl     CH.sub.3                                                                            ClCH.sub.2 CH.sub.2                            11-19      F      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2                             11-20      F      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          11-21      F      Cl     CH.sub.3                                                                            CH.sub.3 SCH.sub.2                             11-22      F      Cl     CH.sub.3                                                                            CH.sub.2CHCH.sub.2                             11-23      F      Cl     CH.sub.3                                                                            CH.sub.2CClCH.sub.2                            11-24      F      Cl     CH.sub.3                                                                            CHCCH.sub.2                                    11-25      F      Cl     CH.sub.3                                                                            CHCCH(CH.sub.3)                                11-26      F      Cl     CH.sub.3                                                                            cC.sub.5 H.sub.9                               11-27      F      Cl     CH.sub.3                                                                            CH.sub.3 CO                                    11-28      F      Cl     CH.sub.3                                                                            CH.sub.3 NHCO                                  11-29      F      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CO                             11-30      F      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CH.sub.2                       11-31      F      Cl     CH.sub.3                                                                            CH.sub.3 OOCCH.sub.2                           11-32      F      Cl     CH.sub.3                                                                            CH.sub.3 SO.sub.2                              11-33      H      Cl     H     (CH.sub.3).sub.2 CH                            11-34      H      Cl     H     ClCH.sub.2 CH.sub.2                            11-35      H      Cl     H     CH.sub.3 OCH.sub.2                             11-36      H      Cl     H     CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          11-37      H      Cl     H     CH.sub.3 SCH.sub.2                             11-38      H      Cl     H     CH.sub.2CHCH.sub.2                             11-39      H      Cl     H     CH.sub.2CClCH.sub.2                            11-40      H      Cl     H     CHCCH.sub.2                                    11-41      H      Cl     H     CHCCH(CH.sub.3)                                11-42      H      Cl     H     cC.sub.5 H.sub.9                               11-43      H      Cl     H     CH.sub.3 CO                                    11-44      H      Cl     H     CH.sub.3 NHCO                                  11-45      H      Cl     H     C.sub.6 H.sub.5 CO                             11-46      H      Cl     H     C.sub.6 H.sub.5 CH.sub.2                       11-47      H      Cl     H     CH.sub.3 OOCCH.sub.2                           11-48      H      Cl     H     CH.sub.3 SO.sub.2                              11-49      H      Cl     CH.sub.3                                                                            (CH.sub.3).sub.2 CH                            11-50      H      Cl     CH.sub.3                                                                            ClCH.sub.2 CH.sub.2                            11-51      H      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2                             11-52      H      Cl     CH.sub.3                                                                            CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2          11-53      H      Cl     CH.sub.3                                                                            CH.sub.3 SCH.sub.2                             11-54      H      Cl     CH.sub.3                                                                            CH.sub.2CHCH.sub.2                             11-55      H      Cl     CH.sub.3                                                                            CH.sub.2CClCH.sub.2                            11-56      H      Cl     CH.sub.3                                                                            CHCCH.sub.2                                    11-57      H      Cl     CH.sub.3                                                                            CHCCH(CH.sub.3)                                11-58      H      Cl     CH.sub.3                                                                            cC.sub.5 H.sub.9                               11-59      H      Cl     CH.sub.3                                                                            CH.sub.3 CO                                    11-60      H      Cl     CH.sub.3                                                                            CH.sub.3 NHCO                                  11-61      H      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CO                             11-62      H      Cl     CH.sub.3                                                                            C.sub.6 H.sub.5 CH.sub.2                       11-63      H      Cl     CH.sub.3                                                                            CH.sub.3 OOCCH.sub.2                           11-64      H      Cl     CH.sub.3                                                                            CH.sub.3 SO.sub.2                              11-65      F      Br     H     (CH.sub.3).sub.2 CH                            11-66      F      F      H     (CH.sub.3).sub.2 CH                            11-67      Cl     Cl     H     (CH.sub.3).sub.2 CH                            ______________________________________                                    

                                      TABLE 12                                    __________________________________________________________________________     ##STR18##                                                                    Compound                                                                      No.   X  Y  R.sup.1                                                                          R.sup.2  R.sup.18                                                                             R.sup.19                                                                          R.sup.20                                   __________________________________________________________________________    12-1  F  Cl H  (CH.sub.3).sub.2 CH                                                                    CH.sub.3                                                                             CH.sub.3                                                                          H                                          12-2  F  Cl H  CH.sub.3 OCH.sub.2                                                                     CH.sub.3                                                                             CF.sub.3                                                                          H                                          12-3  F  Cl H  CHCCH.sub.2                                                                            CH.sub.2 CHCH.sub.2                                                                  CH.sub.3                                                                          H                                          12-4  F  Cl H  CH.sub.3 CO                                                                            CH.sub.3                                                                             CF.sub.3                                                                          H                                          12-5  F  Cl H  CH.sub.3 OOCCH.sub.2                                                                   CH.sub.3                                                                             CH.sub.3                                                                          H                                          12-6  F  Cl CH.sub.3                                                                         CH.sub.3 CH.sub.2 CHCH.sub.2                                                                  CH.sub.3                                                                          H                                          12-7  H  Cl H  (CH.sub.3).sub.2 CH                                                                    CH.sub.3                                                                             CF.sub.3                                                                          H                                          12-8  H  Cl CH.sub.3                                                                         CH.sub.3 CO                                                                            CH.sub.3                                                                             CF.sub.3                                                                          H                                          __________________________________________________________________________

                  TABLE 13                                                        ______________________________________                                         ##STR19##                                                                    (compound wherein Q is Q-13.)                                                 Com-                                                                          pound                                                                         No.   X     Y     R.sup.1                                                                            R.sup.2  R.sup.18 R.sup.21                                                                           R.sup.22                        ______________________________________                                        13-1  F     Cl    H    (CH.sub.3).sub.2 CH                                                                    CH.sub.3 H    H                               13-2  F     Cl    H    CH.sub.3 CO                                                                            CH.sub.3 H    H                               13-3  F     Cl    H    CH.sub.3 OCH.sub.2                                                                     CH.sub.2 CHCH.sub.2                                                                    H    CH.sub.3                        13-4  F     Cl    H    CHCCH.sub.2                                                                            CH.sub.3 CH.sub.3                                                                           CH.sub.3                        13-5  F     Cl    H    CH.sub.3 OOCCH.sub.2                                                                   CH.sub.3 H    H                               13-6  F     Cl    CH.sub.3                                                                           CH.sub.3 CH.sub.3 H    H                               13-7  H     Cl    CH.sub.3                                                                           CH.sub.3 CO                                                                            CH.sub.3 H    Cl                              13-8  H     Cl    H    CH.sub.3 OCH.sub.2                                                                     CH.sub.2 CHCH.sub.2                                                                    H    H                               ______________________________________                                    

The compound 2!, which is a starting compound used in the production ofthe present compounds, can be produced by reacting a phenol compound ofthe formula: ##STR20## wherein X, Y, Q and R¹ are each as defined above,with a compound of the formula:

    R.sup.2 --D.sup.1                                            8!

wherein R² is as defined above; and D¹ is chlorine, bromine, iodine, C₁-C₄ alkylsulfonyloxy such as methanesulfonyloxy, or benzenesulfonyloxywhich may be optionally substituted with at least one C₁ -C₄ alkylgroup, C₁ -C₄ alkoxy group or halogen atom, such as p-toluenesulfonyloxyor benzenesulfonyloxy.

The reaction is usually effected in a solvent in the presence of a base.The reaction temperature is usually in the range of <20° to therefluxing temperature of the solvent. The reaction time is usually inthe range of a moment to 48 hours. The amounts of the reagents to beused in the reaction are usually 1 to 10 moles of the compound 8! andusually 1 mole to an excess of the base, per mole of the compound 7!.

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as petroleum ether and hexane; aromatic hydrocarbons such astoluene and xylene; halogenated hydrocarbons such as chloroform,1,2-dichloroethane, chlorobenzene and o-dichlorobenzene; ethers such asdiethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran andethylene glycol dimethyl ether; ketones such as acetone, methyl isobutylketone and cyclohexanone; esters such as ethyl acetate and diethylcarbonate; nitro compounds such as nitroethane and nitrobenzene;nitriles such as acetonitrile and isobutyronitrile; tertiary amines suchas pyridine, triethylamine, N,N-dimethylaniline, N,N-diethylaniline andN-methylmorpholine; acid amides such as formamide,N,N-dimethyl-formamide and acetamide; sulfur compounds such asdimethylsulfoxide and sulfolane; and mixtures thereof.

Examples of the base which can be used include inorganic bases such aspotassium carbonate, sodium hydroxide and potassium hydroxide; metalhydrides such as sodium hydride and potassium hydride; organic basessuch as triethylamine, diisopropylethylamine, pyridine and4-dimethylaminopyridine; and mixtures thereof.

After completion of the reaction, the reaction mixture is poured intowater, and the precipitated crystals are collected by filtration, or thereaction mixture is subjected to ordinary post-treatments such asextraction with an organic solvent and concentration, followed by, ifnecessary, subsequent purification such as chromatography orrecrystallization. Thus, the desired compounds can be isolated.

The compound 3! can be produced by reacting the compound 7! with anepoxidizing agent.

The reaction is usually effected in a solvent. The reaction temperatureis usually in the range of -20° to 150° C., preferably 0° to 60° C. Thereaction time is usually in the range of a moment to 48 hours. Theamount of the epoxidizing agent to be used in the reaction is usually 1to 5 moles per mole of the compound 7!.

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as petroleum ether and hexane; fatty acids such as formic acid andacetic acid; and halogenated hydrocarbons such as methylene chloride,chloroform and 1,2-dichloroethane. Examples of the epoxidizing agentinclude peracids such as perbenzoic acid, m-chloroperbenzoic acid,peracetic acid and trifluoroperacetic acid.

After completion of the reaction, the reaction mixture is treated, ifnecessary, with a reducing agent such as aqueous sodium thiosulfatesolution or aqueous sodium sulfite solution, followed by ordinarypost-treatments such as extraction with an organic solvent andconcentration, and if necessary, subsequent purification such asrecrystallization. Thus, the compound 3! can be isolated.

The compound 7! can be produced by the method described in, for example,U.S. Pat. No. 4,881,967 or JP-A 156787/1988, or by reacting a compoundof the formula: ##STR21## wherein X, Y, R¹ and Q are each as definedabove, without any solvent or in a solvent, usually at 20° to 300° C.,preferably 100° to 250° C., usually for 0.5 to 48 hours.

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as petroleum ether and hexane; aromatic hydrocarbons such astoluene, xylene and m-isobutylbenzene; halogenated hydrocarbons such aschloroform, 1,2-dichloroethane, chlorobenzene and o-dichlorobenzene;ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane,tetrahydrofuran and ethylene glycol dimethyl ether; ketones such asacetone, methyl isobutyl ketone and cyclohexanone; fatty acids such asformic acid and acetic acid; alcohols such as methanol, ethanol andethylene glycol; esters such as ethyl acetate and diethyl carbonate;nitro compounds such as nitroethane and nitrobenzene; nitriles such asacetonitrile and isobutyronitrile; tertiary amines such as pyridine,triethylamine, N,N-dimethylaniline, N,N-diethylaniline andN-methylmorpholine; acid amides such as formamide, N,N-dimethylformamideand acetamide; sulfur compounds such as dimethylsulfoxide and sulfolane;water; and mixtures thereof.

After completion of the reaction, the reaction mixture is poured intowater, and the precipitated crystals are collected by filtration, or thereaction mixture is subjected to ordinary post-treatments such asextraction with an organic solvent and concentration, followed by, ifnecessary, subsequent purification such as chromatography, distillationor recrystallization. Thus, the desired compound can be isolated.

The compound 9! can be produced according to the method described in,for example, JP-A 41466/1988, JP-A 156787/1988, JP-A 264489/1988, JP-A181283/1987 or EP-517181-A, or as disclosed in any reference cited inthese specifications and publications.

The present compounds have excellent herbicidal activity, and some ofthem exhibit excellent selectivity between crop plants and unfavorableweeds. In particular, the present compounds have herbicidal activityagainst various unfavorable weeds as recited below, which may causetrouble in the foliar treatment and soil treatment on upland fields.Polygonaceae:

wild buckwheat (Polygonum convolvulus), pale smartweed (Polygonumlapathifolium), Pennsylvania smartweed (Polygonum pensylvanicum),ladysthumb (Polygonum persicaria), curly dock (Rumex crispus), broadleafdock (Rumex obtusifolius), Japanese knotweed (Polygonum cuspidatum)Portulacaceae:

common purslane (Portulaca oleracea) Caryophyllaceae:

common chickweed (Stellaria media) Chenopodiaceae:

common lambsquarters (Chenopodium album), kochia (Kochia scoparia)Amaranthaceae:

redroot pigweed (Amaranthus retroflexus), smooth pigweed (Amaranthushybridus) Crusiferae:

wild radish (Raphanus raphanistrum), wild mustard (Sinapis arvensis),shepherdspurse (Capsella bursa-pastoris) Leguminosae:

hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia),Florida beggarweed (Desmodium tortuosum), white clover (Trifoliumrepens) Malvaceae:

velvetleaf (Abutilon theophrasti), prickly sida (Sida spinosa) Viola:

field pansy (Viola arvensis), wild pansy (Viola tricolor) Rubiaceae:

catchweed bedstraw (cleavers) (Galium aparine) Convolvulaceae:

ivyleaf morningglory (Ipomoea hederacea), tall morningglory (Ipomoeapurpurea), entireleaf morningglory (lpomoea hederacea var.integriuscula), pitted morningglory (Ipomoea lacunosa), field bindweed(Convolvulus arvensis) Labiatae:

red deadnettle (Lamium purpureum), henbit (Lamium amplexicaule)Solanaceae:

jimsonweed (Datura stramonium), black nightshade (Solanum nigrum)Scrophulariaceae:

birdseye speedwell (Veronica persica), ivyleaf speedwell (Veronicahederaefolia) Compositae:

common cocklebur (Xanthium pensylvanicum), common sunflower (Helianthusannuus), scentless chamomile (Matricaria inodora), corn marigold(Chrysanthemum segetum), pineappleweed (Matricaria matricarioides),common ragweed (Ambrosia artemisiifolia), giant ragweed (Ambrosiatrifida), horseweed (Erigeron canadensis), Japanese mugwort (Artemisiaprinceps), tall goldenrod (Solidago altissima) Boraginaceae:

field forget-me-not (Myosotis arvensis) Asclepiadaceae:

common milkweed (Asclepias syriaca) Euphorbiaceae:

sun spurge (Euphorbia helioscopia), spotted spurge (Euphorbia maculata)Gramineae:

barnyardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis),giant foxtail (Setaria faberi), large crabgrass (Digitaria sanguinalis),goosegrass (Eleusine indica), annual bluegrass (Poa annua), blackgrass(Alopecurus myosuroides), wild oat (Avena fatua), johnsongrass (Sorghumhalepense), quackgrass (Agropyron repens), downy brome (Bromustectorum), bermudagrass (Cynodon dactylon), fall panicum (Panicumdichotomiflorum), Texas panicum (Panicum texanum), shattercane (Sorghumvulgare) Commelinaceae:

common dayflower (Commelina communis) Equisetaceae:

field horsetail (Equisetum arvense) Cyperaceae:

rice flatsedge (Cyperus iria), purple nutsedge (Cyperus rotundus),yellow nutsedge (Cyperus esculentus)

Further, some of the present compounds have no problematic phytotoxicityon main crops such as corn (Zea mays), wheat (Triticum aestivum), barley(Hordeum vulgare), rice (Oryza sativa), sorghum (Sorghum bicolor),soybean (Glycine max), cotton (Gossypium spp.), sugar beet (Betavulgaris), peanut (Arachis hypogaea), sunflower (Helianthus annuus) andcanola (Brassica napus); garden crops such as flowers and ornamentalplants; and vegetable crops.

The present compounds can attain effective control of unfavorable weedsin the no-tillage cultivation. Further, some of them exhibit noproblematic phytotoxicity on crop plants such as soybean, corn andwheat.

The present compounds have herbicidal activity against variousunfavorable weeds as recited below under the flooding treatment on paddyfields. Gramineae:

barnyardgrass (Echinochloa oryzicola, Echinochloa crus-galli)Scrophulariaceae:

common falsepimpernel (Lindernia procumbens) Lythraceae:

Rotala indica, Ammannia multiflora Elatinaceae:

Elatine triandra Cyperaceae:

smallflower umbrellaplant (Cyperus difformis), hardstem bulrush (Scirpusjuncoides), needle spikerush (Eleocharis acicularis), Cyperus serotinus,Eleocharis kuroguwai Pontederiaceae:

Monochoria vaginalis Alismataceae:

Sagittaria pygmaea, Sagittaria trifolia, Alisma canaliculatumPotamogetonaceae:

roundleaf pondweed (Potamogeton distinctus) Umbelliferae:

Oenanthe javanica

Further, some of the present compounds have no problematic phytotoxicityon transplanted paddy rice or directly-sowed paddy rice.

The present compounds can attain effective control of variousunfavorable weeds in orchards, grasslands, lawns, forests, waterways,canals or other non-cultivated lands.

The present compounds also have herbicidal activity against variousaquatic plants such as water hyacinth (Eichhornia crassipes), which willgrow in waterways, canals or the like.

When the present compound is used as an active ingredient of herbicides,it is usually mixed with solid or liquid carriers or diluents,surfactants and other auxiliary agents, and formulated into emulsifiableconcentrates, wettable powders, flowables, granules, concentratedemulsions, water-dispersible granules, solutions or other formulations.

Each of these formulations may contain the present compound as an activeingredient at an amount of 0.001% to 90% by weight, preferably 0.003% to80% by weight, based on the total weight of the formulation.

Examples of the solid carrier or diluent include fine powders orgranules of the following materials: mineral matters such as kaolinclay, attapulgite clay, bentonite, terra alba, pyrophyllite, talc,diatomaceous earth and calcite; organic substances such as walnut shellpowder; water-soluble organic substances such as urea; inorganic saltssuch as ammonium sulfate; and synthetic hydrated silicon oxide. Examplesof the liquid carrier or diluent include aromatic hydrocarbons such asmethylnaphthalene, phenylxylylethane and alkylbenzenes (e.g., xylene);alcohols such as isopropanol, ethylene glycol and 2-ethoxyethanol;esters such as phthalic acid dialkyl esters; ketones such as acetone,cyclohexanone and isophorone; mineral oils such as machine oil;vegetable oils such as soybean oil and cotton seed oil;dimethylsulfoxide, N,N-dimethylformamide, acetonitrile,N-methylpyrrolidone, water, and the like.

Examples of the surfactant used for emulsification, dispersing orspreading include surfactants of the anionic type, such asalkylsulfates, alkylsulfonates, alkylarylsulfonates,dialkylsulfosuccinates and phosphates of polyoxyethylene alkylarylether; and surfactants of the nonionic type, such as polyoxyethylenealkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylenepolyoxypropylene block copolymers, sorbitan fatty acid esters andpolyoxyethylene sorbitan fatty acid esters.

Examples of the auxiliary agent used for formulation includeligninsulfonates, alginates, polyvinyl alcohol, gum arabic,carboxymethyl cellulose (CMC) and isopropyl acid phosphate (PAP).

The present compound is usually formulated and used for pre-emergence orpost-emergence control of unfavorable weeds by soil treatment, foliartreatment or flooding treatment on upland fields or paddy fields. Thesoil treatment includes soil surface treatment and soil incorporation.The foliar treatment includes application over the plants and directedapplication to the weeds to keep any chemical off the crop foliage.

In some cases, the present compound can be used in combination withother herbicides to enhance its herbicidal activity. Further, thepresent compound can also be used in combination with insecticides,acaricides, nematocides, fungicides, plant growth regulators,fertilizers, soil improver, and the like.

When the present compound is used as an active ingredient of herbicides,the application amount is usually in the range of 0.5 to 10,000 g,preferably 1 to 5000 g, per hectare, although it may vary depending uponthe prevailing weather conditions; formulation type used, applicationtiming, application method, soil involved, crop and weed species, andthe like. In the case of emulsifiable concentrates, wettable powders,flowables, concentrated emulsions, water-dispersible granules orsolutions, the formulation is usually applied at a prescribed amountafter diluted with water having a volume of about 10 to 5000 liters perhectare, if necessary, with the addition of an adjuvant such as aspreading agent. In the case of granules, some types of flowables orsolutions, the formulation is usually applied as such without anydilution.

Examples of the adjuvant include, in addition to the above-recitedsurfactants, polyoxyethylene resin acids (esters), ligninsulfonates,abietates, dinaphthylmethanedisulfonates, crop oil concentrates andvegetable oils such as soybean oil, corn oil, cotton seed oil andsunflower oil.

The present compound can be used as an active ingredient of harvestingaids such as defoliants and desiccating agents for cotton (Gossypiumspp.) and desiccating agents for potato (Solanum tuberosum). In thatcase, the present compound is usually formulated in the same manner asthe case where it is used as an active ingredient of herbicides, andused alone or in combination with other harvesting aids for foliartreatment before the harvesting of crops.

The present invention will be further illustrated by the followingProduction Examples, Formulation Examples and Test examples, which arenot to be construed to limit the scope thereof.

The following will describe Production Examples of the presentcompounds. In these Production Examples, the present compounds aredesignated by the respective compound numbers shown in Tables 1 to 13.

PRODUCTION EXAMPLE 1

To 0.58 g of 1-(4-chloro-6-fluoro-3-hydroxy-2-(2,3-epoxy-2-methylpropyl)phenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dionewere added 5 ml of pyridine and 5 ml of acetic anhydride, and themixture was stirred at room temperature for 2 hours. After completion ofthe reaction, the reaction mixture was concentrated, and the residue wassubjected to preparative thin layer silica gel chromatography, whichafforded 0.5 g of the present compound 8-71.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 1.13 (3×1/2 H, s), 1.16 (3×1/2 H,s), 2.39 (3 H, s), 2.47 (2H, m), 2.30-2.60 (1H, m), 2.97 (1/2 H, d,J=1.52 Hz), 3.08 (1/2 H, d, J=15 Hz), 3.54 (3H, s), 6.30 (1/2 H, s),6.36 (1/2 H, s), 7.30 (1/2 H, d, J=8.7 Hz), 7.31 (1/2 H, d, J=8.6 Hz)

PRODUCTION EXAMPLE 2

First, 0.75 g ofN-(3-acetyloxy-2-allyl-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimidewas dissolved in 10 ml of chloroform, to which 1.0 g ofm-chloroperbenzoic acid was added at 0° C., and the mixture was stirredfor 19 hours, while slowly warming to room temperature. After completionof the reaction, the reaction mixture was subjected to phase separationwith ethyl acetate and aqueous sodium sulfite solution, and the organiclayer was successively washed with saturated aqueous sodium bicarbonatesolution and water, dried and concentrated. The residue was preparativethin layer silica gel chromatography, which afforded 0.50 g of thepresent compound 1-21.

¹ H-NMR δ(ppm) 60 MHz, CDCl₃ /TMS!: 1.60-1.90 (4H, m), 2.30 (3H, s),2.30-2.50 (4H, m), 2.55-3.00 (3H, m), 7.60 (1H, d, J=9 Hz)

PRODUCTION EXAMPLE 3

In this example, 0.7 g of the present compound 1-71 was obtained in thesame manner as described in Production Example 2, except that 0.7 g ofN-(3-acetyloxy-4-chloro-6-fluoro-2-(2-methyl-2-propenyl)phenyl)-3,4,5,6-tetrahydrophthalimideand 0.7 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 1.50 (3H, s), 1.80-1.90 (4H, m),2.39 (3H, s), 2.40-2.50 (4H, m), 2.48 (2H, s), 2.70 (2H, d, J=14.9 Hz),2.92 (2H, d, J=14.9 Hz), 7.26 (1H, d, J=8.6 Hz)

PRODUCTION EXAMPLE 4

In this example, 0.36 g of the present compound 1-76 was obtained in thesame manner as described in Production Example 2, except that 0.5 g ofN-(4-chloro-6-fluoro-3-(4-methoxyphenylcarbonyloxy)-2-(2-methyl-2-propenyl)phenyl)-3,4,5,6-tetrahydrophthalimideand 0.6 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 1.41 (3H, s), 1.65-1.90 (4H, m),2.35-2.50 (6H, m), 2.78 (1H, d, J=14 Hz), 2.90 (1H, d, J=14 Hz), 3.91(3H, s), 7.02 (2H, d, J=7.0 Hz), 7.30 (1H, d, J=8.6 Hz), 8.18 (2H, d,J=7.0 Hz)

PRODUCTION EXAMPLE 5

In this example, 0.6 g of the present compound 1-79 was obtained in thesame manner as described in Production Example 2, except that 0.6 g ofN-(4-chloro-6-fluoro-3-(methylaminocarbonyloxy)-2-(2-methyl-2-propenyl)phenyl)-3,4,5,6-tetrahydrophthalimideand 0.5 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 1.59 (3H, s), 1.75-1.90 (4H, m),2.35-2.55 (6H, m), 2.77 (1H, d, J=14.9 Hz), 2.85-3.00 (3H, m), 5.22 (1H,br), 7.24 (1H, d, J=8.7 Hz)

PRODUCTION EXAMPLE 6

In this example, 0.46 g of the present compound 1-80 was obtained in thesame manner as described in Production Example 2, except that 0.6 g ofN-(4-chloro-3-(dimethylaminocarbonyloxy)-6-fluoro-2-(2-methyl-2-propenyl)phenyl)-3,4,5,6-tetra-hydrophthalimideand 0.5 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 1.68 (3H, s), 1.75-1.90 (4H, m),2.35-2.45 (4H, m), 2.49 (2H, s), 2.78 (1H, d, J=14.8 Hz), 2.89 (1H, d,J=1.48 Hz), 3.05 (3H, s), 3.18 (3H, s), 7.22 (1H, d, J=8.6 Hz)

PRODUCTION EXAMPLE 7

In this example, 0.84 g of the present compound 1-95 was obtained in thesame manner as described in Production Example 2, except that 0.9 g ofN-(4-chloro-6-fluoro-3-methanesulfonyloxy-2-(2-methyl-2-propenyl)phenyl)-3,4,5,6-tetrahydrophthalimideand 0.8 g of m-chloroperbenzoic acid were used as the startingmaterials.

1H-NMR δ(ppm) 300 MHz, CDCl₃ /TMS!: 1.22 (3H, s), 1.75-1.90 (4H, m),2.35-2.50 (6H, m), 2.96 (1H, d, J=15.3 Hz), 3.33 (1H, d, J=15.3 Hz),3.47 (3H, s), 7.28 (1H, d, J=8.4 Hz)

PRODUCTION EXAMPLE 8

In this example, 0.52 g of the present compound 8-21 was obtained in thesame manner as described in Production Example 2, except that 0.7 g of1-(3-acetyloxy-2-allyl-4-chloro-6-fluorophenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione and 0.43 g ofm-chloroperbenzoic acid were used as the starting materials.

¹ H-NMR δ(ppm) 300 MHz, CDCl₃ /TMS!: 2.40 (3H, s), 2.60-2.95 (5H, m),3.55 (3H, s), 6.33 (1/2H, s), 6.36 (1/2H, s), 7.30 (1H, d, J=8.6 Hz)

PRODUCTION EXAMPLE 9

In this example, 0.69 g of the present compound 8-22 was obtained in thesame manner as described in Production Example 2, except that 0.9 g of1-(2-allyl-4-chloro-6-fluoro-3-propionyloxyphenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 0.95 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 1.32 (3H, t, J=7.6 Hz), 2.38 (2H,m), 2.60-3.00 (5H, m), 3.55 (3H, s), 6.33 (1/2H, s), 6.36 (1/2H, s),7.31 (1H, d, J=8.6 Hz)

PRODUCTION EXAMPLE 10

In this example, 0.8 g of the present compound 8-24 was obtained in thesame manner as described in Production Example 2, except that 0.8 g of1-(2-allyl-4-chloro-6-fluoro-3-pivaloyloxyphenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tretrahydropyrimidine-2,6-dioneand 1.0 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 300 MHz, CDCl₃ /TMS!: 1.42 (9H, s), 2.35-3.00 (5H, m),6.33 (1/2H, s), 6.36 (1/2H, s), 7.30 (1H, d, J=8.6 Hz)

PRODUCTION EXAMPLE 11

In this example, 0.54 g of the present compound 8-25 was obtained in thesame manner as described in Production Example 2, except that 0.8 g of1-(2-allyl-3-benzoyloxy-4-chloro-6-fluorophenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione and 1.0 g ofm-chloroperbenzoic acid were used as the starting materials.

¹ H-NMR δ(ppm) 300 MHz, CDCl₃ /TMS!: 2.30-3.00 (5H, m), 3.56 (3H, s),6.34 (1/2H, s), 6.38 (1/2H, s), 7.35 (1H, d, J=8.7 Hz), 7.48-7.72 (3,m), 8.10-8.24 (2H, m)

PRODUCTION EXAMPLE 12

In this example, 2.26 g of the present compound 8-32 was obtained in thesame manner as described in Production Example 2, except that 2.5 g of1-(2-allyl-3-benzyloxy-4-chloro-6-fluorophenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 2.0 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 2.35 (m), 2.59 (m), 2.80-3.06 (m),(these correspond to 5H in total), 3.55 (3H, s), 4.98 (1H, d, J=10.8Hz), 5.05 (1H, d, J=10.8 Hz), 6.33 (1/2H, s), 6.36 (1/2H, s), 7.29 (1H,d, J=8.9 Hz), 7.36-7.50 (5H, m)

PRODUCTION EXAMPLE 13

In this example, 0.6 g of the present compound 8-51 was obtained in thesame manner as described in Production Example 2, except that 0.63 g of1-(4-chloro-6-fluoro-3-methoxy-2-(2-methyl-2-propenyl)phenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 0.7 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 1.14 (3×1/2H, s), 1.18 (3×1/2H, s),2.34 (1/2H, d, J=14.7 Hz), 2.50 (2H, m), 2.62 (1/2H, d, J=14.8 Hz), 3.15(1/2H, d, J=14.8 Hz), 3.30 (1/2H, d, J=14.7 Hz), 3.54 (3H, s), 3.87 (3H,s), 6.29 (1/2H, s), 6.37 (1/2H, s), 7.23 (1/2H, d, J=8.8 Hz), 7.24(1/2H, d, J=8.8 Hz)

PRODUCTION EXAMPLE 14

In this example, 0.25 g of the present compound 8-53 was obtained in thesame manner as described in Production Example 2, except that 0.25 g of1-(4-chloro-6-fluoro-3-isopropoxy-2-(2-methyl-2-propenyl)phenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 0.2 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 1.09 (3×1/2H, s), 1.13 (3×1/2H, s),1.23-1.43 (6H, m), 2.34 (1/2H, d, J=14.6 Hz), 2.48 (2H, m), 2.63 (1/2H,d, J=14.8 Hz), 3.22 (1/2H, 14.8 Hz), 3.39 (1/2H, d, J=14.6 Hz), 3.53(3H, s), 4.52 (1H, m), 6.27 (1/2H, s), 6.37 (1/2H, s), 7.23 (1/2H, d,J=8.8 Hz), 7.24 (1/2H, d, J=8.8 Hz)

PRODUCTION EXAMPLE 15

In this example, 0.46 g of the present compound 8-56 was obtained in thesame manner as described in Production Example 2, except that 0.5 g of1-(4-chloro-6-fluoro-3-methoxymethyloxy-2(2-methyl-2-propenyl)phenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione and 0.5 g ofm-chloroperbenzoic acid were used as the starting materials.

¹ H-NMR δ(ppm) 300 MHz, CDCl₃ /TMS!: 1.16 (3×1/2H, s), 1.19 (3×1/2H, s),2.37 (1/2H, d, J=14.8 Hz), 2.48 (2H, m), 2.49 (1/2H, d, J=15.0 Hz), 3.28(1/2H, d, J=15.0 Hz), 3.47 (1/2H, d, J=14.8 Hz), 3.54 (3H, s), 3.60 (3H,s), 5.06-5.16 (2H, m), 6.29 (1/2H, s), 6.36 (1/2H, s), 7.24 (1H, d,J=8.8 Hz)

PRODUCTION EXAMPLE 16

First, 1.0 g of1-(4-chloro-6-fluoro-3-hydroxy-2-(2,3-epoxy-2-methyl-propyl)phenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dionewas dissolved in 10 ml of dimethylsulfoxide and 5 ml of aceticanhydride, and the mixture was stirred at room temperature for 24 hours.After completion of the reaction, the reaction mixture was subjected tophase separation with ethyl acetate and saturated aqueous sodiumbicarbonate solution, and the organic layer was washed with water, driedand concentrated. The residue was preparative thin layer silica gelchromatography, which afforded 0.9 g of the present compound 8-60.

¹ H-NMR δ(ppm) 60 MHz, CDCl₃ /TMS!: 1.15 (3H, s), 2.0-3.0 (7H, m), 3.55(3H, s), 5.12 (2H, s), 6.30 (1/2H, s), 6.33 (1/2H, s), 7.30 (1H, d, J=8Hz).

PRODUCTION EXAMPLE 17

In this example, 0.5 g of the present compound 8-66 was obtained in thesame manner as described in Production Example 2, except that 0.5 g of1-(4-chloro-6-fluoro-2-(2-methyl-2-propenyl)-3-propargyloxyphenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 0.32 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 1.14 (3×1/2H, s), 1.19 (3×1/2H, s),2.37 (1/2H, d, J=14.8 Hz), 2.50 (2H, m), 2.58 (1H, t, J=2.1 Hz), 2.70(1/2H, d, J=14.9 Hz), 3.28 (1/2H, d, J=14.9 Hz), 3.50 (1/2H, d, J=14.8Hz), 3.54 (3H, s), 4.72-4.76 (2H, m), 6.29 (1/2H, s), 6.37 (1/2H, s),7.24 (1/2H, d, J=8.9 Hz), 7.25 (1/2H, d, J=8.5 Hz)

PRODUCTION EXAMPLE 18

In this example, 0.8 g of the present compound 8-74 was obtained in thesame manner as described in Production Example 2, except that 0.8 g of1-(4-chloro-6-fluoro-2-(2-methyl-2-propenyl)-3-trimethylacetyloxyphenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 1.0 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 1.18 (3H, s), 1.42 (9H, s),2.30-3.00 (4H, m), 3.54 (3H, s), 6.29 (1/2H, s), 6.35 (1/2H,s), 7.28(1/2H, s), 8.8 Hz), 7.29 (1/2H, d, J=8.6 Hz)

PRODUCTION EXAMPLE 19

In this example, 0.8 g of the present compound 8-75 was obtained in thesame manner as described in Production Example 2, except that 0.8 g of1-(3-benzoyloxy-4-chloro-6-fluoro-2-(2-methyl-2-propenyl)phenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 1.0 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 300 MHz, CDCl₃ /TMS!: 1.14 (3H, s), 2.43 (2H, m), 2.65(1H, br), 3.01 (1H, br), 3.55 (3H, s), 6.31 (1/2H,s), 6.38 (1/2H, s),7.35 (1/2H, d, J=8.6 Hz), 7.36 (1/2H, d, J=8.6 Hz), 7.45-7.72 (3H, m),8.09-8.25 (2H, m)

PRODUCTION EXAMPLE 20

In this example, 0.33 g of the present compound 8-76 was obtained in thesame manner as described in Production Example 2, except that 0.5 g of1-(4-chloro-6-fluoro-3-(4-methoxybenzoyloxy)-2-(2-methyl-2-propenyl)phenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 0.6 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 300 MHz, CDCl₃ /TMS!: 1.15 (3H, s), 2.44 (2H, m), 2.65(1H, br), 3.03 (1H, br), 3.56 (3H, s), 3.92 (3H,s), 6.32 (1/2H, s), 6.38(1/2H, s), 7.03 (2H, d, J=8.9 Hz), 7.34 (1/2H, d, J=8.6 Hz), 7.35 (1/2H,d, J=8.6 Hz), 8.19 (2H, d, J=8.9 Hz)

PRODUCTION EXAMPLE 21

In this example, 0.6 g of the present compound 8-79 was obtained in thesame manner as described in Production Example 2, except that 0.6 g of1-(4-chloro-6-fluoro-3-methylaminocarbonyloxy-2-(2-methyl-2-propenyl)phenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 0.5 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 300 MHz, CDCl₃ /TMS!: 1.14 (3×1/2H, s), 1.17 (3×1/2H, s),2.39 (1/2H, d, J=15.1 Hz), 2.49 (2H, m), 2.62 (1/2H, d, J=15.1 Hz), 2.92(3×1/2H, s), 2.94 (3×1/2H, s), 2.99 (1/2H, d, J=15.1 Hz), 3.11 (1/2H, d,J=15.1 Hz), 3.54 (3H, s), 5.23 (1H, br), 6.30 (1/2H, s), 6.36 (1/2H, s),7.27 (1H, d, J=8.6 Hz)

PRODUCTION EXAMPLE 22

In this example, 0.6 g of the present compound 8-80 was obtained in thesame manner as described in Production Example 2, except that 0.6 g of1-(4-chloro-3-di-methylaminocarbonyloxy-6-fluoro-2-(2-methyl-2-propenyl)phenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 0.5 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 300 MHz, CDCl₃ /TMS!: 1.15 (3×1/2H, s), 1.18 (3×1/2H, s),2.40 (1/2H, d, J=15.4 Hz), 2.49 (2H, s), 2.62 (1/2H, d, J=15.2 Hz), 2.97(1/2H, d, J=15.2 Hz), 3.04 (3H, s), 3.09 (1/2H, d, J=15.4 Hz), 3.17 (3H,s), 3.54 (3H, s), 6.29 (1/2H, s), 6.36 (1/2H, s), 7.28 (1H, d, J=7.8 Hz)

PRODUCTION EXAMPLE 23

In this example, 0.6 g of the present compound 8-86 was obtained in thesame manner as described in Production Example 2, except that 0.6 g of1-(4-chloro-6-fluoro-3-methoxycarbonylmethyloxy-2-(2-methyl-2-propenyl)phenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 0.34 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 60 MHz, CDCl₃ /TMS!: 1.20 (3H, s), 2.40-2.80 (1H, m),2.45 (2H, s), 3.23-3.50 (1H, m), 3.50 (3H, s), 3.78 (3H, s), 4.60 (2H,s), 6.21 (1/2H, s), 6.30 (1/2H, s), 7.15 (1H, d, J=8 Hz)

PRODUCTION EXAMPLE 24

In this example, 0.8 g of the present compound 8-87 was obtained in thesame manner as described in Production Example 2, except that 1.0 g of1-(4-chloro-3-ethoxycarbonylmethyloxy-6-fluoro-2-(2-methyl-2-propenyl)phenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 0.8 g of m-chloroperbenzoic acid were used as the startingmaterials.

1H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 1.17 (3×1/2H, s), 1.21 (3×1/2H, s),1.32 (3H, t, J=7.1 Hz), 2.33 (1/2H, d, J=14.7 Hz), 2.48 (2×1/2H, s),2.50 (2×1/2H, s), 2.67 (1/2H, d, J=14.8 Hz), 3.41 (1/2H, d, J=14.8 Hz),3.53 (3H, s), 3.61 (1/2H, d, J=14.7 Hz), 3.29 (2H, q, J=7.1 Hz),4.51-4.79 (2H, m), 6.29 (1/2H, s), 6.37 (1/2H, s), 7.23 (1/2H, d, J=8.7Hz), 7.24 (1/2H, d, J=8.6 Hz)

PRODUCTION EXAMPLE 25

In this example, 0.4 g of the present compound 8-92 was obtained in thesame manner as described in Production Example 2, except that 1.0 g of1-(4-chloro-3-(1-ethoxycarbonylethyloxy)-6-fluoro-2-(2-methyl-2-propenyl)phenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 0.6 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 300 MHz, CDCl₃ /TMS!: 1.10-1.32 (6H, m), 1.47-1.68 (3H,m), 2.42-2.53 (4H, m), 3.53 (3H, s), 4.11-84.29 (2H, m), 4.91-4.99 (1m),6.27 (1/2H, s), 6.35 (1/2H, s), 7.22 (1/2H, d, J=8.7 Hz), 7.23 (1/2H, d,J=8.6 Hz)

PRODUCTION EXAMPLE 26

In this example, 0.43 g of the present compound 8-95 was obtained in thesame manner as described in Production Example 2, except that 0.5 g of1-(4-chloro-6-fluoro-3-methanesulfonyloxy-2-(2-methyl-2-propenyl)phenyl)-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 0.5 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 1.20 (3×1/2H, s), 1.24 (3×1/2H, s),2.47 (2×1/2H, s), 2.48 (2×1/2H, s), 2.53 (1/2H, d, J=15.6 Hz), 2.83(1/2H, d, J=15.7 Hz), 3.38 (1/2H, d, J=15.7 Hz), 3.48 (3H, s), 3.53 (3H,s), 3.57 (1/2H, d, J=15.6 Hz), 6.30 (1/2H, s), 6.35 (1/2H, s), 7.32(1/2H, d, J=8.4 Hz), 7.33 (1/2H, d, J=8.4 Hz)

PRODUCTION EXAMPLE 27

In this example, 0.4 g of the present compound 8-121 was obtained in thesame manner as described in Production Example 2, except that 0.5 g of1-(3-acetyloxy-2-allyl-4-chlorophenyl)-3-methyl-4-fluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dioneand 0.5 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 2.40 (3H, s), 2.04-3.00 (5H, m),3.54 (3H, s), 6.33 (1/2H, s), 6.37 (1/2H, s), 7.02 (1/2H, d, J=8.5 Hz),7.04 (1/2H, d, J=8.5 Hz), 7.49 (1H, d, J=8.5 Hz)

PRODUCTION EXAMPLE 28

In this example, 0.57 g of the present compound 1-59 was obtained in thesame manner as described in Production Example 2, except that 0.58 g ofN-(4-chloro-6-fluoro-3-methoxyethoxymethoxy-2-(2-methyl-2-propenyl)phenyl)-3,4,5,6-tetrahydrophthalimideand 0.34 g of m-chloroperbenzoic acid were used as the startingmaterials.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 1.17 (3H, s), 1.78-1.90 (4H, m),2.35-2.50 (4H, m), 2.47 (2H, s), 2.87 (1H, d, J=15 Hz), 3.16 (1H, d,J=15 Hz), 3.40 (3H, s), 3.60 (2H, m), 3.95 (2H, m), 5.20 (2H, q, J=4Hz), 7.19 (1H, d, J=8 Hz)

The following will describe Reference Production Example of the compound3! which is a starting compound used in the production of the presentcompounds.

REFERENCE PRODUCTION EXAMPLE 1

First, 50 g of 1-4-chloro-6-fluoro-3-hydroxy-2-(2-methyl-2-propenyl)phenyl!-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dionewas dissolved in 500 ml of chloroform, to which 30.0 g ofm-chloroperbenzoic acid was added, and the reaction was allowed toproceed at 60° C. for 4.5 hours. After completion of the reaction, thereaction mixture was cooled to room temperature and subjected to phaseseparation with chloroform and aqueous sodium sulfite solution. Theorganic layer was successively washed with saturated aqueous sodiumbicarbonate solution and water, dried and concentrated. The residue wasrecrystallized to afford 46 g of 1-4-chloro-6-fluoro-3-hydroxy-2-(2,3-epoxy-2-methylpropyl)phenyl!-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione.

¹ H-NMR δ(ppm) 60 MHz, CDCl₃ /TMS!: 1.29 (1/2×3H, s), 1.31 (1/2×3H, s),2.75 (3H, m), 3.10 (1H, m), 3.58 (3H, s), 6.31 (1H, s), 7.20 (1H, d, J=8Hz), 7.45 (1H, s)

The following will describe Reference Production Example of the compound2! which is a starting compound used in the production of the presentcompounds.

REFERENCE PRODUCTION EXAMPLE 2

First, 1.0 g of 1-4-chloro-6-fluoro-3-hydroxy-2-(2-methyl-2-propenyl)phenyl!-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dionewas dissolved in 15 ml of N,N-dimethylformamide, to which 0.43 g ofpotassium carbonate and 0.4 ml of methyl bromoacetate were added, andthe mixture was stirred at room temperature for 30 minutes. Aftercompletion of the reaction, the reaction mixture was poured into waterand extracted with diethyl ether. The organic layer was dried andconcentrated. The residue was subjected to silica gel chromatography,which afforded 1.0 g of 1-4-chloro-6-fluoro-3-methoxycarbonylmethyloxy-2-(2-methyl-2-propenyl)phenyl!-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione.

¹ H-NMR δ(ppm) 250 MHz, CDCl₃ /TMS!: 1.60 (3H, s), 3.34 (1H, d, J=15.4Hz), 3.49 (1H, d, J=15.4 Hz), 3.52 (3H, s), 3.81 (3H, s), 4.45 (1H, s),4.60 (2H, s), 4.66 (1H, s), 6.32 (1H, s), 7.22 (1H, d, J=8.6 Hz)

The following will describe Reference Production Example of the compound7! which is a starting compound used in the production of the presentcompounds.

REFERENCE PRODUCTION EXAMPLE 3

First, 21.6 g of 1-4-chloro-2-fluoro-5-(2-methyl-2-propenyloxy)phenyl!-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dionewas dissolved in 50 ml of N,N-diethylaniline, and the solution washeated under reflux for 4 hours. After completion of the reaction, thereaction mixture was cooled to room temperature and extracted withdiethyl ether. The extract was washed with diluted hydrochloric acid,dried and concentrated. The residue was subjected to silica gelchromatography (eluent; hexane: ethyl acetate=2:1), which 19.5 g of 1-4-chloro-6-fluoro-3-hydroxy-2-(2-methyl-2-propenyl)phenyl!-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione.

¹ H-NMR δ(ppm) 60 MHz, CDCl₃ /TMS!: 1.60 (3H, s), 3.28 (2H, s), 3.48(3H, s), 4.4-4.6 (1H, m), 4.6-4.8 (1H, m), 5.76 (1H, s), 6.36 (1H, s),7.09 (1H, d, J=10 Hz)

The following will describe Reference Production Examples of thecompound 9!.

REFERENCE PRODUCTION EXAMPLE 4

To a suspension of 1.4 g ofN-(4-chloro-2-fluoro-5-allyloxy)phenyl-N'-methylthiourea and 0.5 g ofsodium acetate in 20 ml of toluene is added 1.0 g of3-bromo-1,1,1-trifluoroacetone, and the mixture is stirred under reflux.After completion of the reaction, the reaction mixture is poured intowater. The organic layer is separated, washed with water, dried withmagnesium sulfate and concentrated. The residue is mixed with 10 ml ofconcentrated sulfuric acid, and the mixture is stirred. The reactionmixture is poured onto ice and extracted with ethyl acetate. The organiclayer is washed, dried with magnesium sulfate and concentrated. Theresidue is subjected to silica gel chromatography to give a compound ofthe formula: ##STR22##

REFERENCE PRODUCTION EXAMPLE 5

To a suspension of 0.4 g ofN-(4-chloro-2-fluoro-5-allyloxy)phenyl-N'-methylthiourea and 0.12 g ofsodium acetate in 5 ml of ethanol is added 0.22 g of bromoacetic acid,and the mixture is stirred under reflux for 2 hours. After completion ofthe reaction, the reaction mixture is poured into water and extractedwith ethyl acetate. The organic layer is washed with saturated sodiumhydrogencarbonate solution, dried with magnesium sulfate andconcentrated. The residue is subjected to silica gel chromatography togive a compound of the formula: ##STR23##

The following will describe Formulation Examples. In these FormulationExamples, the present compounds are designated by the respectivecompound numbers shown in Tables 1 to 13, and parts are by weight.

FORMULATION EXAMPLE 1

Fifty parts of each of the present compounds 1-21, 1-76, 1-79, 1-95,8-22, 8-25, 8-51, 8-56, 8-75, 8-80, 8-92, 8-121 and 8-175, 3 parts ofcalcium ligninsulfonate, 2 parts of sodium laurylsulfate and 45 parts ofsynthetic hydrated silicon oxide are well pulverized and mixed to give awettable powder for each compound.

FORMULATION EXAMPLE 2

Ten parts of each of the present compounds 1-32, 1-71, 1-80, 8-6, 8-21,95 and 8-171, 14 parts of polyoxyethylene styryl phenyl ether, 6 partsof calcium dodecylbenzenesulfonate, 35 parts of xylene and 35 parts ofcyclohexanone are well mixed to give an emulsifiable concentrate foreach compound.

FORMULATION EXAMPLE 3

Two parts of each of the present compounds 1-21, 1-32, 1-71, 1-76, 1-79,1-95, 8-6, 8-22, 8-25, 8-32, 8-53, 8-56, 8-60, 8-66, 8-75, 8-76, 8-79,8-121, 8-171 and 8-175, 2 parts of synthetic hydrated silicon oxide, 2parts of calcium ligninsulfonate, 30 parts of bentonite and 64 parts ofkaoline clay are well pulverized and mixed, to which water is added, andthe mixture is well kneaded, granulated and dried to give a granule foreach compound.

The following Test Examples will demonstrate that the present compoundsare useful as active ingredients of herbicides. The present compoundsare designated by the respective compound numbers shown in Tables 1 to13.

The herbicidal activity was evaluated at 6 levels with indices of 0 to5, i.e., designated by the numeral "0", "1", "2", "3", "4" or "5",wherein "0" means that there was no or little difference in the degreeof germination or growth between the treated and the untreated testplants at the time of examination, and "5"means that the test plantsdied complete or their germination or growth was completely inhibited.The herbicidal activity is excellent when rated at "5" or "4" butinsufficient when rated at "3" or lower.

TEST EXAMPLE 1

Soil surface treatment

Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth werefilled with soil, and the seeds of ivyleaf morningglory (Ipomoeahederacea) and velvetleaf (Abutilon theophrasti) were sowed therein.Each of the test compounds 1-21, 1-79, 8-6, 8-21, 8-22, 8-25, 8-51,8-56, 8-60, 8-71, 8-75, 8-79 and 8-80 was formulated into anemulsifiable concentrate according to Formulation Example 2, which wasdiluted with water to a prescribed concentration. The dilution wasuniformly sprayed over the soil surface in the pots with a sprayer at avolume of 1000 liters per hectare. In this treatment, each of the testcompounds was applied at an amount of 500 grams per hectare. After thespraying, the test plants were grown in a greenhouse for 19 days, andthe herbicidal activity was examined.

As a result, it was found that all the test compounds exhibited thehighest herbicidal activity "5" to both ivyleaf morningglory andvelvetleaf.

TEST EXAMPLE 2

Foliar treatment

Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth werefilled with soil, and the seeds of velvetleaf (Abutilon theophrasti)were sowed therein and grown in a greenhouse for 12 days. Each of thetest compounds 1-79, 1-80, 8-6, 8-21, 8-56, 8-60, 8-71 8-79, 8-80 and8-92 was formulated into an emulsifiable concentrate according toFormulation Example 2, which was diluted with water containing aspreading agent to a prescribed concentration. The dilution wasuniformly sprayed over the foliage of the test plants with a sprayer ata volume of 1000 liters per hectare. In this treatment, each of the testcompounds was applied at an amount of 500 grams per hectare. After thespraying, the test plants were grown in the greenhouse for 19 days, andthe herbicidal activity was examined.

As a result, it was found that all the test compounds exhibited thehighest herbicidal activity "5" to velvetleaf.

TEST EXAMPLE 3

Flooding treatment

Cylindrical plastic pots of 9 cm in diameter and 11 cm in depth werefilled with soil, and the seeds of barnyardgrass (Echinochloa oryzicola)were sowed therein. These pots were flooded to form a paddy field, andthe test plants were grown in a greenhouse for 7 days. Each of the testcompounds 1-32, 1-71, 1-76, 1-79, 1-95, 8-6, 8-21, 8-22, 8-25, 8-32,8-53, 8-56, 8-60, 8-66, 8-71, 8-75, 8-76, 8-79, 8-121, 8-171 and 8-175was formulated into an emulsifiable concentrate according to FormulationExample 2, which was diluted with water to a prescribed concentration.The dilution was applied to the water surface in the pots with a syringeat a volume of 5000 liters per hectare. In this treatment, each of thetest compounds was applied at an amount of 250 grams per hectare. Afterthe application, the test plants were grown in the greenhouse for 19days, and the herbicidal activity was examined.

As a result, it was found that all the test compounds exhibited thehighest herbicidal activity "5" to barnyardgrass.

What is claimed is:
 1. A compound of the formula: ##STR24## wherein X ishydrogen, fluorine or chlorine; Y is fluorine, chlorine or bromine;R¹ ishydrogen or C₁ -C₃ alkyl; R² is C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₆alkoxy (C₁ -C₆) alkyl, C₁ -C₆ alkoxy (C₁ -C₆) alkoxy (C₁ -C₆) alkyl, C₁-C₆ alkylthio (C₁ -C₆) alkyl, C₃ -C₆ alkenyl, C₃ -C₆ haloalkenyl, C₃ -C₆alkynyl, C₃ -C₆ haloalkynyl or C₃ -C₆ cycloalkyl; or R² is a group ofthe formula:

    --COR.sup.3

wherein R³ is C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, phenyl which may beoptionally substituted with at least one halogen atom, C₁ -C₃ alkylgroup or C₁ -C₃ alkoxy group; or a group of the formula:

    --NR.sup.4 R.sup.5

wherein R⁴ and R⁵ are independently hydrogen, C₁ -C₆ alkyl or C₁ -C₆haloalkyl; or R² is a group of the formula: ##STR25## wherein n is aninteger of 1 to 5; R⁶ is hydrogen, halogen, C₁ -C₃ alkyl or C₁ -C₃alkoxy; or R² is a group of the formula:

    --CR.sup.7 R.sup.8 COOR.sup.9

wherein R⁷ and R⁸ are independently hydrogen or C₁ -C₃ alkyl; R⁹ ishydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl or C₃ -C₆ cycloalkyl; or R² isa group of the formula:

    --SO.sub.2 R.sup.10

wherein R¹⁰ is C₁ -C₆ alkyl or C₁ -C₆ haloalkyl; or phenyl which may beoptionally substituted with at least one C₁ -C₃ alkyl group; and --Q isone of the groups Q-7 to Q-8 of the following formulae: ##STR26##wherein A¹ is oxygen or sulfur; R¹³ is hydrogen, halogen or C₁ -C₃alkyl; R¹⁴ is C₁ -C₃ alkyl which may be optionally substituted with atleast one halogen atom; and R¹⁵ is hydrogen, C₁ -C₆ alkyl, C₃ -C₆alkenyl, C₃ -C₆ alkynyl, amino or benzyl.
 2. A compound of the formula:##STR27## wherein X is hydrogen, fluorine or chlorine; Y is fluorine,chlorine or bromine;R¹ is hydrogen or C₁ -C₃ alkyl; R² is C₁ -C₆ alkyl,C₁ -C₆ haloalkyl, C₁ -C₆ alkoxy (C₁ -C₆) alkyl, C₁ -C₆ alkoxy (C₁ -C₆)alkoxy (C₁ -C₆) alkyl, C₁ -C₆ alkylthio (C₁ -C₆) alkyl, C₃ -C₆ alkenyl,C₃ -C₆ haloalkenyl, C₃ -C₆ alkynyl, C₃ -C₆ haloalkynyl or C₃ -C₆cycloalkyl; or R² is a group of the formula:

    --COR.sup.3

wherein R³ is C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, phenyl which may beoptionally substituted with at least one halogen atom or C₁ -C₃ alkylgroup; or a group of the formula:

    --NR.sup.4 R.sup.5

wherein R⁴ and R⁵ are independently hydrogen, C₁ -C₆ alkyl or C₁ -C₆haloalkyl; or R² is a group of the formula: ##STR28## wherein n is aninteger of 1 to 5; R⁶ is hydrogen, halogen or C₁ -C₃ alkyl; or R² is agroup of the formula:

    --CR.sup.7 R.sup.8 COOR.sup.9

wherein R⁷ and R⁸ are independently hydrogen or C₁ -C₃ alkyl; R⁹ ishydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl or C₃ -C₆ cycloalkyl; or R² isa group of the formula:

    SO.sub.2 R.sup.10

wherein R¹⁰ is C₁ -C₆ alkyl or C₁ -C₆ haloalkyl; or phenyl which may beoptionally substituted with at least one C₁ -C₃ alkyl group; and --Q isone of the groups Q-7 to Q-8 of the following formulae: ##STR29##wherein A¹ is oxygen or sulfur; R¹³ is hydrogen, halogen or C₁ -C₃alkyl; R¹⁴ is C₁ -C₃ alkyl which may be optionally substituted with atleast one halogen atom; and R¹⁵ is hydrogen, C₁ -C₆ alkyl, C₃ -C₆alkenyl, C₃ -C₆ alkynyl, amino or benzyl.
 3. A compound according toclaim 1, wherein --Q is a group of the formula Q-8.
 4. A compoundaccording to claim 1, wherein X is hydrogen or fluorine; Y is chlorine;R² is C₁ -C₆ alkyl, C₁ -C₆ alkoxy (C₁ -C₆) alkyl, C₁ -C₆ alkoxy (C₁ -C₆)alkoxy (C₁ -C₆) alkyl, C₁ -C₆ alkylthio (C₁ -C₆) alkyl, C₃ -C₆ alkenylor a group of the formula: ##STR30## wherein R³ is C₁ -C₆ alkyl, phenylwhich may be optionally substituted with at least one C₁ -C₃ alkoxygroup; or a group of the formula: --NR⁴ R⁵, wherein R⁴ and R⁵ areindependently hydrogen or C₁ -C₆ alkyl; R⁷ and R⁸ are independentlyhydrogen or C₁ -C₃ alkyl; R⁹ is C₁ -C₆ alkyl; R¹⁰ is C₁ -C₆ alkyl; --Qis a group of the formula Q-8; A¹ is oxygen; R¹³ is hydrogen; R¹⁴ is C₁-C₃ alkyl which may be optionally substituted with at least one halogenatom; and R¹⁵ is C₁ -C₆ alkyl.
 5. A compound according to claim 1wherein R¹ is hydrogen or methyl, R² is acetyl, benzoyl,methylthiomethyl or methoxymethyl.
 6. A compound according to claim 1,wherein X is fluorine; Y is chlorine; R¹ is methyl; R² is acetyl ormethylthiomethyl; --Q is a group of the formula Q-8; A¹ is oxygen; R¹³is hydrogen; R¹⁴ is trifluoromethyl; and R¹⁵ is methyl.
 7. A herbicidalcomposition comprising a herbicidally effective amount of the compoundaccording to claim 1, and an inert career or diluent.
 8. A herbicidalcomposition according to claim 7, wherein the amount of the compound is0.001% to 90% by weight based on the total weight of the composition. 9.A method for exterminating unfavorable weeds, which comprises applying aherbicidally effective amount of the compound according to claim 1 to anarea where the unfavorable weeds grow or will grow.
 10. A methodaccording to claim 9, wherein the application amount of the compound is0.5 to 10,000 g/ha.
 11. A compound according to claim 4, wherein R¹ ishydrogen or methyl, R² is acetyl, benzoyl, methylthiomethyl ormethoxymethyl.